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Celebrating the 2023 Hutch cohort

Seven small businesses complete the intensive two-year program

Congratulations to our 4th Hutch cohort! The future is bright for our 7 founders and we’re excited to see the mark they will make on government tech.

At our Dec. 2023 graduation, Hutch board member and VP of Digital Solutions, Julie Meloni told our graduates to focus on meaningful and lasting change in this journey.

“There are so many things to change, but there are so many things that are working in government. Remember that you’ve got to bring people along as you change.”

The 4th Hutch cohort is part of an alumni network of now more than a dozen companies building and growing successful digital services firms.

Mechanicode founder Emmanuel Apau (Class of ’23) has seen tremendous company growth in the two-year program.

“I’m a computer scientist, not a business owner. So when I joined Hutch I was a party of one. I saw this as an experiment. Can I start a business? Through the things that went on along the way and through my fellow Hutch members, all of that was a benefit to grow from a company of one to now a company of five.

Meet our 2023 Hutch cohort:

  • BlackRose Cyber Solutions, founded by 21-year Army Cyber Warfare Veteran Hector Peralta, is a cybersecurity firm specializing in penetration testing. 
  • Code360, Inc, founded by Makesh Pitchaipillai, is an 8(a) and HUBZone certified IT Services company providing software development and consulting services. Code360, Inc specializes in advanced Health IT, Cloud, Software Development, Business Intelligence, and Open Standards.
  • greiBO solutions, founded by Phillip Stokes, helps its customers to understand its environment and how to secure their enterprise through data driven decisions. greiBO supports corporate capabilities and big data analytics through data management via Nifi, Hadoop, and more. Phillip Stokes, greiBO Solutions LLC
  • Mechanicode, founded by a former USDS engineer Emmanuel Apau, is an agile SDB HUBZone MBE/DBE Digital services firm providing comprehensive DevSecOps, Cloud Native Engineering, IT Modernization & Automation, and Software Development consulting services.
  • Pixel Creative Services, LLC, founded by Christina Alchus, is a EDWOSB certified design agency that provides custom professional designs, easy-to-use products, and helpful technology solutions for its DoD clients and partners. 
  • Tall Glass Media, founded by Eric Murphy, is a full-service digital design studio that crafts thought-provoking and creative experiences through strategy, research, and world-class design. Tall Glass Media is dedicated to helping visionary organizations reach their communication goals and use design as a catalyst for social impact.
  • Triton Technology, founded by Marvin Douglas, is a digital services company located in Baltimore delivering cloud, security, agile project management, and automation services to government healthcare agencies and private sector.

The Hutch journey

“These folks have been through the wringer for the last two years. It is no small feat to be a small business owner. And they have committed the past two years to being in our incubator program. They are growing their businesses and growing themselves as professional leaders,” said Stephanie Chin, Hutch Program Manager.

At Hutch, we believe increasing the number of minority and women-led companies in the digital services world is critical to building technology that better serves the public good. Most Hutch companies are engaged in contracting or subcontracting work before they even leave the program.

“It isn’t easy building a business. It’s scary and challenging and filled with ups and downs. I am so very proud of all our Hutch graduates,” said Fearless CEO Delali Dzirasa. “The federal marketplace is a $100B industry. It needs more leaders like our graduates. They bring unique experiences, perspectives, and skills to the table. It’s our honor to help our founders build their roadmap to scale their businesses for success.”

With 20+ companies currently in the Hutch cohort portfolio, Hutch has a goal to grow to 45 digital services firms by 2025.

Strategic financial management: Tips from an expert.

As a small business owner, prioritizing strategic financial management is one of the most important things you can do for your business.

But you likely started your business because you believe in the work you’re doing. Not because you’re a finance expert.

At Hutch, we recognize not everyone has a background in finance. Which is why we give our cohort companies a strong foundation of support on their financial journey. This happens over the course of 3 intensive financial management sessions throughout our 24-month program.

But we believe in empowering our entire community, not just those who can join our program.

Which is why our expert finance coach and Fearless CFO, Ryan Hemminger, recently hosted a virtual office hour. (Sign up for our newsletter to find out when we’re hosting our next expert office hour)

Now we’re sharing Ryan’s responses to attendee’s burning financial planning questions.

The strategic financial management journey.

When you first begin your financial planning journey, it can be hard to know where to start. And as your company grows, your financial strategy and planning needs will dramatically change.

“From a financial planning perspective,” says Ryan, “your company will go through distinct phases.” And in each, your company will need to prioritize and focus on different areas.

Phase 1: Inflows over outputs.

In the first stage of your business, your business’s inflows — which include all of the income your company generates through work — will be more important than your outflows.

By maintaining strong inflows, you’ll be able to keep your business afloat and eventually grow into phase two.

Phase 2: Budgeting.

During this stage, you’ll create a budget. You’ll then use your budget to think through what the next 12 to 18 months will look like. And you’ll strategize how you’ll measure your progress against that plan.

This budget will help you determine if your business is making enough money and ensure you’re on the right path.

Phase 3: Long-term forecasting.

During this phase, you’ll focus on your 5-10 year forecast. 

As you’re undergoing this long-term forecasting, you’ll want to ask “where is the cash going to come from that will fuel your operations?” says Ryan. And, as you consider that question, you’ll want to focus on the return on investment (ROI) for the capital that you’ll bring into the company.

Cash flow: Your strategic financial management through-line.

As you go through each of the previous phases, one of the major through-lines that will be consistently important is cash flow. 

This is because “cash flow, especially as a small business, is the lifeblood of your company,” says Ryan.

Essentially, cash flow is the moving of money in and out of your business.

Dealing with slow-to-pay primes.

Being a government contractor means you’re likely going to work with primes who will be slow to pay you. Pay schedules are different for all primes.

And, considering how tight margins can be for small businesses, a late payment can negatively impact your business.

Start a conversation.

The first thing Ryan recommends when your prime is slow to pay, is talking to them.

“Look at your cash flow,” says Ryan. “From there, talk to your prime and let them know where you stand.”

Letting them know that you have cash flow challenges, and that you don’t have access to the same debt facilities that they might, could lead to quicker payments.

Some primes, like Fearless, will work with you. But with larger primes, you’ll have less ability to influence their payments and contracts.

Be diligent in your planning.

When you’re unable to influence your prime’s payment schedule, you’ll have to be more diligent in your planning. 

You’ll also need to ensure that you have a credit facility that will support the delays in payment. This will likely mean that, when you get a line of credit from the bank, you’ll want to ask them for “a big enough line to support you in the event you don’t get paid for 30, 60, or 90 days,” says Ryan.

Staying on top of your planning and thinking ahead when you get a line of credit will help offset some of the issues that arise when a prime is slow to pay.

Getting and using loans.

One of the most important aspects of running a small business — and the strategic financial management that goes with it —  is getting the capital to ensure you can keep it running. 

And one way to get capital is by acquiring loans.

Knowing the information banks will need, and how you can use your loan strategically, will help you have a much smoother loan process.

Getting a business loan.

Figuring out what you need to do to secure a loan can be complicated. 

After all, loans help ensure your business has the money it needs to thrive. But if you’ve never gotten a business loan before, it can be hard to know where to start.

1. Get your credit in order.

When you’re preparing to take out a loan, it’s important to remember that your bank account isn’t your business’s bank account. This means you’ll need to create a separate business bank account and credit card if you haven’t already.

This is important, because getting your business’s credit in order — and establishing your credit history — is the first thing you need to do before taking out a loan.

Use the credit card as much as you can — though you can’t use it for everything — and then pay it off every month to establish your business’s credit history.

2. Get your financial statements.

Once your credit is in order, you’ll need to have financial statements that you can show to the bank or lender.

There are a variety of tools you can use to put these statements together. But, according to Ryan, QuickBooks is the easiest to use and therefore usually the best option when you’re starting out.

Whatever tool you choose, use it to get your company’s financial statements, income statements, and balance sheets. Which are all documents that your bank will need to approve your loan.

Once you have these, the bank will look at your statements, along with your cash flow forecast and your credit history to determine whether they’ll loan to you and how much.

3. Take the number they offer, then renegotiate in a year.

Finally, after the bank has reviewed your information and offered you a loan, Ryan recommends you take whatever amount they’re willing to give you. Even though it will likely be a small loan, you just need to ensure it’s sustainable for the next 12 months.

After the 12 months are over, you can go back to your banker and ask them for a bigger loan. And then do that again every year to steadily increase the amount you’re borrowing.

Using the loan strategically.

Now that you’ve secured a loan and you’re further along with your strategic financial management journey, you might be wondering what to use the money for.

And if you ask 100 CFOs this question, you’ll get 100 different answers.

But Ryan’s general rule of thumb is:

“You want to have at least enough money to cover two pay periods — either in your bank account or through a line of credit.” Because you don’t want to be in a position where an accounting error leads to layoffs.

So, while it might be tempting to use the entirety of the loan to reinvest in your business, remember to save enough to ensure your company can keep functioning even in an emergency situation.

Calculate the ROI to determine how to use your loan.

But what should you do with your loan once you’ve set aside enough to cover two pay periods?

While this is a complicated question, the answer will come down to knowing what your ROI is going to be.

This means that, before making an investment, you’ll need to take the time to understand what your expected outcome is. And then, if you get a different outcome, what you’re going to do about it.

“You’re not in the business of throwing money at problems, or even throwing money at potential wins,” says Ryan. “You have to commit to making the investment that your company can afford.”

Understanding the ROI of using your loan will help you determine which investments your company can actually afford.

Bringing in investors.

Not every business will want or need investors. And the type of business you own will determine when you should seek out investors, if you plan to do so.

When it comes to bringing on investors,

  • Product companies generally need them earlier. And they’ll likely use the capital from investors to expand production or distribution.
  • Services companies will be less likely to need capital early on. Instead, they’ll seek out investors when they’re ready for expansion.

But whether you’re a product or a services company, you should think through your business goals before you bring on investors.

Some organizations, like Fearless, decide that investors don’t fit in with the future they’re envisioning and their strategic financial management journey. Instead, they look at debt vehicles as an alternative.

Debt vehicles can be preferable to investors for a variety of reasons. Whether you’re interested in:

  • Keeping your equity intact,
  • Waiting to bring on investors until your company is more established, 
  • Or taking advantage of low interest loans sponsored by the federal government.

Keeping your options open — and remembering that there are alternative solutions that offer the same outcomes as investors — will help you make the best decision for your company.

Getting investors.

With all this said, even if you decide against getting investors at this stage, you might want to work with some in the future.

If and when you’re ready to do so, the information investors are looking for will depend on if you’re working with equity or debt investors.

Equity investors.

Equity investors financially back your company, and in exchange they receive a stake in the business.

An equity investor will look at your company’s:

  • Profit and loss (P&L) forecast: They’ll specifically focus on your EBITA, which will determine your company’s value.
  • Balance sheet: This will help them ensure that there isn’t anything of concern around your debt or liabilities.
  • Overall forecast: This will help them calculate their ROI.

An equity investors’ goal will likely be to grow your company to a certain point before finding a larger private equity firm that will buy them out and invest in you. Which means their priority will be to calculate how fast they’ll make a profit after investing in your company.

Debt investors.

Unlike equity investors, who get a stake in your company in exchange for financial backing, working with debt investors involves borrowing money directly.

And while equity investors focus on your business’ overall forecast to get a sense of their ROI, debt investors want to know if you’ll be able to pay back their loan.

Because of this, they’ll look at your company’s:

  • Cash flow,
  • Income statements,
  • Balance sheet.

These will help them determine whether you have enough free cash flow to cover their debt services.

Using your goals to determine what to do with your profits.

Knowing how much money you should reinvest in your business, and how much you should take out as profit, is an important aspect of strategic financial management. But it’s also a difficult decision to make. And the option you choose will depend on what your goals are as an entrepreneur.

For example, you might want to hit a specific benchmark and then maintain that size until you’re ready to leave the company. When that’s the case, you might be able to take a lot of the profit out of the company.

Or, your goal might be more impact focused. And in that case, if you take all the money out in profit, you won’t have enough resources to make an impact through your work.

And if you understand your goals, but you’re still wondering how you’ll know when you’ve made enough profit or generated enough wealth, Ryan recommends asking an advisor.

Whether you’re thinking of one day retiring as a business owner, or you hope to eventually sell your company, you should get an advisor who will work through the entirety of your financial plan. And who will help you understand how to get to the outcome you want.

Expanding your team.

When you’re looking to expand your workforce, the first thing you’ll want to do is make sure you can afford another employee. Which will require you to look at your cash flow. 

But if, after looking at your cash flow, you realize you can’t afford to bring someone on, there are other options.

For example, you can “bring in a 1099,” says Ryan. “Or, if they have their own company, subcontract them. That way you can better manage your payment schedule and your cash flow.”

This sort of financial decision making, especially early in your company’s strategic financial management journey, will be critical to your long-term success.

Bring on employees when you can actually afford it.

If you find that you can’t afford to bring on an employee, it might be tempting to offer equity as an alternative form of compensation. 

But, Ryan says that’s a big mistake a lot of early entrepreneurs make.

After all, you don’t want to be in a position where you bring someone on, give them a stake in your company, and then they decide to move on. Because then you’ll be expected to do all the work alone, while missing out on a portion of your company.

So, while offering equity might seem like a viable solution, it’s better to protect your equity and save it for when you really need it.

Wait for the right time to invest in a CFO.

Although a CFO is a valuable executive and team member, Ryan recommends small businesses should take their time before investing in one.

This is because a CFO is going to add a layer of administration a smaller organization can’t afford. And, when you’re smaller, you likely don’t need the kind of in-depth financial planning a CFO can offer.

Before getting a CFO, there are other options for financial experts you can utilize:

  • Bookkeepers — You likely won’t need a bookkeeper permanently on-staff when you first start your company. Instead, you should outsource this work. Eventually, when you get a few million dollars in revenue, you can consider bringing on a part-time bookkeeper.
  • Accountants — An accountant is always necessary. And if you don’t have one, you’ll want to get one. “Don’t file your own taxes,” says Ryan. “I can’t stress enough that you should be paying someone to file them for you. It’s money well spent.”
  • DCAA advisors — If you’re in government contracting, you might also want to consider getting an advisor who can help you with your DCAA compliance. And will help you ensure your filings are in order. Like the bookkeeper, this advisor should be outsourced.

And if you don’t have any of these people on your team, then you’re not ready for a CFO.

But eventually, you’ll want to bring on a CFO. And Ryan recommends you do so just before you start to grow dramatically.

A CFO will be most valuable at this point because they’ll be able to:

  • Help you develop your growth plan,
  • Give you pushback on whether or not that growth plan is reasonable,
  • Understand if you’re making reasonable decisions along the way.

By waiting to bring on a CFO until your company is actually ready for them, you’ll be able to take full advantage of their expertise, while saving your company money.

Get more strategic financial management tips from Ryan.

Whether you’re a new company or a seasoned business looking to expand, strategic financial planning will be critical to your success.

But knowing where to start can be hard.

If you’d like more tips from Ryan, check out his “4 tips for strategic financial planning.”

Hutch Accepting Founders for 2025 cohort

Government IT is a huge market. Hutch is here to help founders of color and women entrepreneurs tap into it. 

In 2022, the White House’s requested IT budget was more than $100 billion. The government aims to set aside 23% of federal contracting dollars for small businesses every year. If they reach that goal, it amounts to over $25 billion for small business government IT services.

But how do small businesses looking to make a mark on government digital services and impact government grow in an ocean of large-scale IT projects and big organizations.

Hutch is a 24-month program that gives entrepreneurs a blueprint for building successful digital service firms in the B2G space. We think of Hutch as a home-base for our members, giving them a foundation of support so they can grow in the government contracting space without getting lost amongst bigger companies in the industry. 

“We realize the access to opportunities, capital, knowledge, information, and a support system is not readily available to founders of color or many women entrepreneurs, especially in the tech ecosystem,” said Hutch coach and Fearless CEO Delali Dzirasa. “Hutch is here to fill that void.”

Since 2019, Hutch has grown its portfolio to include 20 companies across various disciplines.

Seeking entrepreneurs for the next Hutch cohort

Our goal at Hutch is to help digital services companies acquire customers in the multi-billion dollar government IT market.

Applications are now open for the 2025 cohort

We are hosting 5 info sessions this fall to get to know potential participants and share how Hutch can impact them and their business.

  • Tues. October 17th 4:00-5:00pm EST
  • Thurs. October 19th 12:00-1:00pm EST
  • Mon. October 23rd 5:00-6:00pm EST
  • Wed. October 25th 2:00-3:00pm EST
  • Fri. November 3rd 9:00-10:00am EST

Attendance at 1 info session is required to apply for the cohort and have your application reviewed.

We focus on:

  • Entrepreneurs of color/women founders
  • Business to Government contractors who provide these digital services:
    • Design
    • Agile Management
    • Product Development
    • DevSecOps and Compliance
    • Data and Transparency
    • SaaS, PaaS, or IaaS Implementation
  • Impact-driven businesses that want to improve their communities and the world around them

What Hutch offers entrepreneurs:

We think of Hutch as a home-base for our members, giving them a foundation of support so they can grow.

Hutch services:

  • One-on-one mentoring
  • Expert guidance on government contracting
  • Discounted HUBZone, WOSB, EDWOSB and 8(a) Certifications and Consultations
  • Dedicated bank partnership, including support for establishing lines of credit and creating financial projections
  • Benefits specialist who provides coaching and assistance
  • Baltimore office space co-located within Spark and Fearless
  • Lasting relationships, partnerships, & networks

Sign up for an info session and learn how Hutch can help you grow as a founder.

4 tips for strategic financial planning

Strategic financial planning is one of the most important things you can do for your business. 

An effective plan will help you grow in the government contracting space sustainably and successfully. Planning also empowers you to allocate resources effectively, secure funding, manage risks, and set competitive pricing.

But knowing what to prioritize and focus on can be difficult if you’ve never financially managed a business before.

Our expert coach can help guide you on this journey. Ryan Hemminger, Fearless CFO and Hutch finance coach, hosts several intensive sessions on Financial Management as part of our 24-month program. We’re sharing Ryan’s top tips for managing your businesses finances, and mistakes to avoid.

1. Use cash flow projections to track the financial health of your business.


When it comes to effective financial management, you might assume our number one tip would be around pricing or taxes. And, while we do get into those, we wanted to start with the most important information first.

Illustration of coins to represent the importance of financial planning

For Ryan, “cash flow is the most important thing when it comes to strategic financial planning. Your cash flow will tell you whether you’re in business or out of business.” It’s a valuable asset that will help you understand whether your business is thriving or teetering on the edge of solvency.

What is cash flow?

Essentially, cash flow is the moving of money in and out of your business.

According to Ryan, “cash flow tells you when the actual cash occurs in the bank account. It’s how much money is coming in and how much is going out.” 

To keep track of your cash flow, you need to start a new daily habit.

“If you’re not looking at your bank account balance every day, you’re doing it wrong.”

Cash flow projection.

While cash flow shows when funds enter and exit your bank account, a cash flow projection is a financial statement that’s used to predict cash moving in and out of the business. 

Why use cash flow projection?

Using cash flow projection on your strategic financial planning journey will help you:

  • Predict your sales cycle,
  • Plan major purchases or hiring,
  • Establish a break even point,
  • Track liquidity,
  • Determine financing needs.

It can also alert you to financial trouble. If you spot trouble, you can either reduce expenses or access your credit. 

Cash flow projection process.

Your monthly cash flow projection process should involve:

  1. Examining your bank account, 
  2. Logging all revenue, 
  3. Logging all expenses,
  4. Projecting this information out for at least the next quarter; preferably 12 months. 

By following this process, you can spot trouble several months in advance. 

2. Keep pricing consistent and honest.

illustration of a hand holding a coin

Figuring out pricing can feel like a daunting task when you’re new to financial management and managing your own business. But as you build your rate, remember the value of consistency and honesty.

“Whatever pricing methodology you pick when you start your strategic financial planning journey,” says Ryan, “just keep it consistent. Most small businesses find themselves in hot water because they shifted from one opportunity to the next.”

And remember to “be as honest as possible when creating your pricing structure.” Don’t assume you won’t get caught inflating your costs. Because even if you get away with it today, they’ll notice it later.

Common pricing mistakes.

While there’s no standard pricing model that you can use for your strategic financial planning, there are some common pricing mistakes that you can avoid. 

  • Not calculating indirect costs — People often price too low because they forget that there are costs besides their employee’s salaries that are incurred. 
  • Dropping your fee down to zero to win — You’re not a nonprofit, so don’t drop your fee to zero. Doing so will leave you with no flexibility in your contract.
  • Failing to account for administrative hours needed — Failing to account for your—or anyone else’s—time creating and monitoring the bid and other administrative tasks.
  • Failing to justify all the costs — The government will ask you questions about your work, and you will need to justify everything to them. When you do, make sure you’re honest. Because it’s far worse to get caught lying than to tell the truth upfront. 

3. Take advantage of tax credits.

Tax credits are a valuable resource that all small businesses should take advantage of as part of their strategic financial planning. 

Unlike a deduction, which is a reduction of your taxable income, tax credits allow you to subtract from the amount of taxes you owe to the government.

“Tax credits are far more valuable than deductions. And it’s through credits that you’ll save your money.”

But there are a lot of tax credits out there, and it’s not always easy to tell which ones will be valuable to you and your business.

We’ve put together a list of Maryland and federal tax credits to help you begin this process.

Maryland tax credits.

  • Employer Security Clearances Costs (ESCC) — If you’re a small business that does security-based contract work, you can get income tax credits for expenses related to federal security clearance costs, construction of Sensitive Compartmented Information Facilities (SCIFCs), and first-year leasing costs.
  • Buy Maryland Cybersecurity (BMC) — This is specifically for Maryland cybersecurity companies with 50 or fewer employees. It provides an income tax credit of 50% of the purchase price for cybersecurity goods, products, or services from Qualified Maryland Cybersecurity Sellers (QMCS).
  • Enterprise Zone (EZ) — This tax credit is location based, and it provides property and state income tax credits for businesses located in a Maryland Enterprise Zone in return for job creation and investments.
  • Hire Our Veterans — If you’re a small business that hires qualified veterans, you can get a state income tax credit based on the wages you pay to those veteran employees.
  • Maryland Opportunity Zone Enhancement (State Program) — Businesses that are located in federal Opportunity Zones and that meet certain requirements can get enhanced tax credits through the Maryland Department of Commerce’s tax credit programs.
  • Job Creation Tax Credit (JCTC) — You can get state income tax credits of up to $3,000-$5,000 per job by creating a minimum number of new full-time positions in a revitalization area.
  • One Maryland — By investing in an economic development project in a Tier 1 County and creating a minimum number of new jobs, you may qualify for a state income tax credit of up to $5 million. This amount depends on the number of jobs created and amount of eligible costs.
  • Research and Development — If your business has qualified research and development expenditures in Maryland, you might qualify for two state income tax credits: the Basic R&D Tax Credit, and the Growth R&D Tax Credit. 

Federal tax credits.

  • Small Employer Health Insurance Premiums — This tax credit allows you to write off the cost of setting up your medical plan if you’re a small employer. An important note: if you’ve already set up your medical plan, you can’t retroactively apply for this credit.
  • Small Employer Pension Plan Startup Costs — When you set up your 401K, you can get a tax credit for the startup costs. An important note: if you’ve already set up your 401K, you can’t retroactively apply for this credit.
  • Paid FMLA — If you offer paid family and medical leave, you can receive a federal tax credit.

Ask your accountant about tax credits.

If you’re interested in taking advantage of any of these state and federal tax credits as part of your strategic financial planning, we suggest sharing them with your accountant. They’ll be able to help you determine if you’re eligible and whether you should apply for them. 

Also ask your accountant if you can “take advantage of any of these credits historically,” says Ryan. This would help you determine if you need to restate your taxes to apply the credits retroactively. 

4. Bring in experts when you need to.

Icon of hands shaking to symbolize the importnace of partnership in financial planning

When it comes to financial management, you shouldn’t be expected to be an expert. In fact, it’s often better in the long-run to spend the money and hire experts that will help you and your business thrive.

Ryan says three of the most valuable resources you can outsource are:

  1. Insurance brokers,
  2. 401K brokers,
  3. Tax accountants (in fact, you should never do your own taxes).

At Hutch we remind our companies, just because you’re running your own business, doesn’t mean you have to do it alone. And it’s better to bring in experts who can help your business thrive, rather than assuming you can do everything on your own. 

Learn more strategic financial planning tips from the Hutch team.

We understand financial management can feel overwhelming. But these tips from our finance coach will help you on your strategic financial planning journey.

By using cash flow projections, being honest and consistent in pricing, taking advantage of tax credits, and bringing in experts when you need, you’ll be better prepared to grow in the government contracting space sustainably and successfully.

Want to learn more from our experts? Applications are now open for the 2025 class.

Sign up for an info session to learn more!

Hutch company Boostaro helps Fearless bring agile solutions to CMS

The Centers for Medicare and Medicaid Services’ (CMS) Medicaid and the Children’s Health Insurance Program (CHIP) are used by over 93 million people. These programs give access to free or low-cost health insurance to qualifying families, children, pregnant women, seniors, people with disabilities, and people with low incomes.

With millions of people relying on these programs, CMS must be responsive to the needs of their users. To better serve those users, CMS is updating their Medicaid and CHIP (MACPRO) system.

MACPRO receives and processes documents, data, and reports from state and CMS users. And it allows the Center for Medicaid and CHIP Services’ (CMCS) staff to effectively engage with their state partners.

Boostaro — a Hutch cohort company — is partnering with Fearless to assist CMS in their work. Boostaro and Fearless will apply an agile, collaborative, and human-centered design (HCD) approach as they improve CMS’ MACPRO system.

“We’re not building software for the sake of building software,” says Boostaro founder and CEO founder . “We’re building software to make an impact on the everyday citizens that are using this service. And not just at the national level, but even at the state level.”

To assist in this work, Boostaro is providing coaching to CMS individuals and teams on the Scaled Agile Framework (SAFe). This coaching will ensure CMS is set up for success even after the project is over.

“I’m looking forward to figuring out how we can best help CMS move forward on their journey. And to build valuable relationships that will provide optimal results,” says Snehal.

The value of relationship building.

Fearless has worked on various MACPRO projects for CMS since 2020, with this project originally starting without Boostaro on the contract. But this changed when CMS spent two days working in-person with Fearless in their Spark space.

While at Spark, a director in CMS’ Data and Systems Group recognized Snehal, who was in the office for a Hutch session. Having worked together before, the CMS director immediately told Nichole Weems, Fearless’ Health and Sciences Portfolio Director, that they “need Snehal on this project. And he needs to be key to our work.”

Having successfully spearheaded numerous organizational change initiatives that not only improved operational efficiency, but also fostered a culture of continuous improvement, it was clear that Boostaro was perfect for this project.

As Nichole says, “this was one of those magical ‘aha’ moments that happen when people come together. And the customer seeing Snehal at Fearless meant the three of us could come together. This allowed me to better understand what the customer wanted and needed.”

As Snehal says, Boostaro’s “emphasis on meeting teams where they are in their agile journey, and their reputation for collaborative leadership is exactly what CMS was seeking to ensure a smooth and effective transition.”

Boostaro’s addition to the project demonstrates what a powerful combination solid relationship building and good timing can be.

Relearning how to work together.

In addition to updating the MACPRO system, Fearless and Boostaro are training CMS team members on agile and SAFe practices. This work can be challenging in an increasingly asynchronous environment.

“In agile,” Snehal says, “you focus on individuals and interactions over processes and tools.” But post-COVID, processes and tools have only become more important. With tools like Slack and Zoom replacing in-person interactions, it can be difficult to find a way to keep them from driving the things we do.

In this asynchronous world, “people are almost having to relearn how to connect with one another and what the new ways of connection are,” says Snehal. “As a coach, I’m always thinking about ways to adapt to this change. And figure out the best ways to present what we used to coach in-person, virtually.”

But Snehal relishes this work. “This is an opportunity to help CMS, and specifically MACPRO” he says. “By coaching people and providing guardrails, we’ll make sure processes aren’t driving how we think and do things.”

Looking ahead.

As Fearless and Boostaro continue working with CMS, they’re “making sure MACPRO will be a system that’s not only easy for CMS to use, but for the end user as well,” says Snehal.

Hutch graduate supporting Baltimore market revitalization

Points North joins $9+ million Avenue market revitalization

Baltimore’s Avenue Market has been a staple of the City’s Upton community since 1871. To invest in the market’s future, the community hub is undergoing a nearly $10 million redevelopment. Hutch graduate company Points North Studio is leading the branding for the revitalized space.


“The public markets in Baltimore, they have such an incredible history and they’re a staple. They’ve been a place where a lot of folks went for their produce and shopping. Over the years, the markets have grown or scaled back. So Baltimore is in the middle of a revitalization of the markets across the board,” Points North founder and CEO Jessica Watson.

Points North studio owner Jess Watson

For the Avenue Market project, officials aim to rebuild all of the market’s stalls as well as develop space for a demo kitchen and community events.

Community is at the heart of Points North’s work. In developing the market’s brand and telling its story, Watson and her team are telling the story of the neighborhood and the people who shop at the market. Developers have been holding meetings and listening sessions with community groups and Points North will be building on the feedback from the people who use the market.

“It’s about making sure we are bringing a community up with the revitalization as opposed to taking away. It’s important to honor the legacy and history of the generations and generations of people who have had different experiences with the market in their neighborhood.”

Community improvements

At the project’s announcement, Congressman Kweisi Mfume emphasized that the market is part of the fabric of Upton and will once again be a jewel in the area.

“We want to turn this back into a first-class market so that it rivals any other market,” Mfume said. “We’re going to have fresh produce and fresh food, people will come and have an opportunity to gather again and all things that were lacking are going to be put back in place.”

“This revitalization project is an incredible opportunity for Points North Studio to be partners in,” said Hutch program manager Stephanie Chin. “Points North has always had a passion for working with impact-oriented organizations, and this newest project brings an opportunity for Jess and her team to bring their design superpowers to a place that will improve lives for so many Baltimoreans.”

For Points North, their work with the Avenue Market team is part of their growth strategy into more ambitious projects. For 10+ years, the design studio has worked with diverse companies and global foundations to develop brands and marketing that avoids trends and instead focuses on passion.

Points North Looking Ahead:

Moving forward, Watson is looking to take on more large-scale initiatives, like the Avenue Market project, to expand the impact Points North can have on an organization.

“I want to take the same design thinking and creative problem solving we’re known for and see what else we can apply it to. That means sometimes going into a place and being like, this is a dark room, and I don’t know what’s in it yet, but we’re going to get some lights working. And we’re gonna shine the flashlight in different areas. We can take challenges and look at them as opportunities and see how we can get in and where we fit.”

Strategic planning tips from an expert

Finding the time for everything that needs to get done as a small business owner can feel impossible. But annual strategic planning is a powerful tool that can actually help you get time back.

If you’re new to strategic planning though, it can be hard to know where to start. That’s why we hosted an office hour with Fearless’ COO John Foster. During this virtual event, he answered attendees’ burning questions and shared how Fearless uses strategic planning to reach their goals.

The free office hour we offer on a semi-regular basis is a great opportunity for attendees to get tips, ask questions, and learn from someone who has been successfully utilizing strategic planning for his company for many years.

If you want to learn more about strategic planning, read our ultimate annual strategic planning playbook!

What does strategic planning look like at Fearless?

When implementing a new framework like strategic planning, it can be useful to understand how other companies have successfully utilized it.

John says Fearless takes a slightly different approach to strategic planning compared to other companies. Fearless’ strategic planning includes a trimester and end-of-year planning tempo. And both of these sessions include brainstorming around what worked in the past year, what they need in the coming year, and creating outlined ideas and goals from there.

1. Tempo

Planning starts with tempo, and for the Fearless team that comes in the form of trimester planning as opposed to quarterly planning. The executive team sees this as “an intentional speed bump” that forces them to “understand what’s working and what’s not working.”

They also have an end-of-year planning session in the fall. During this the executive team discusses what they’re going to focus on in the course of the following year. However, even before this end-of-year meeting, they’ve already taken the time to outline and write down what their five year goals are.

2. Brainstorming sessions

During these trimester and end-of-year planning sessions, the Fearless team brainstorms around the questions:

  • What went well in the past year?
  • What do they need to do in the coming year?

These questions are purposefully high-level and allow them to focus on ideation. And no idea is wrong, so long as they move Fearless towards their five-year goals.

3. Outlining ideas and creating goals

Finally, company leadership decides, of those generated ideas, what success looks like. They also decide how they’ll measure that success. From there, they work with departments and team members to understand, operationally, how to achieve those goals over the next trimester or year.

If you want to know how other companies have successfully used strategic planning, check out our interview with three Hutch cohort companies.

Outlining your strategic plan

When you’re outlining your strategic plan, John says the biggest lessons he’s learned are to name the authority, ensure goals are cross-cutting, and keep it simple.

1. Name the authority

John emphasizes it’s important in strategic planning sessions to make it explicit and clear who has the final authority to make a decision.

“When you’re not clear about who has the authority to make decisions in that space, you’ll come out of the planning session with no actionable goals,” he says.

2. Make sure goals are cross-cutting

Remember that, when you talk about your goals at the highest level for the year, those initiatives need to be cross-cutting to the organization.

For example, if your goal is to improve recruiting, don’t just delegate this work to your recruiters while everyone else continues with their work as normal. By doing this, you put too much pressure on a single department or individual to move the ball.

Instead, “you have to get people to think and operate collaboratively,” says John.

3. Keep it simple

Finally, remember to keep it simple.

To do this, Fearless creates a spreadsheet and on day one of strategic planning for an upcoming year, the executive team adds as many things that didn’t go well and need to be corrected in the coming year as they can think of. From that, they’re able to see patterns very quickly and can “get to the affinity around where people feel like they need to go, strategically.”

Strategic planning tips for success

John didn’t only focus on how Fearless leverages strategic planning and how you can outline your plan. He also shared useful tips you can use to create a successful strategic plan.

Have a “dreaming session”

The first step in your strategic planning journey should be sitting down and having a “dreaming session.” And during this session, ask yourself “what will the world look like in three years or five years?”

From there, you want to take the time to name what that change looks like and to name what your goal around it looks like.

When you name your goal, make sure you’re intentional about how you measure its success. Doing this will allow you to see whether the goal makes sense or not.

And remember that not every goal and measurement needs to be quantitative, it can be qualitative. So long as you’re measuring, that’s what matters.

For more information on the power of measurable goals, John recommends the book “Measure What Matters” by John Doerr. “It’s a must for anyone who’s trying to grow and scale a company,” he says.

Begin with the end in mind

How you think about strategic planning and the constructs around it will be the same, whether you’re a one or two person company, or even if you have several hundred employees. It’s all about focusing on what you want to accomplish in the next three to five years.

And the best way to do that is to “begin with the end in mind,” as John’s college mentor used to remind him. This means that you should act as if you’re already a company with several hundred employees. This will allow you to instill habits within yourself and your company early on. And this will pay dividends down the road.

Keep it simple

If you’re just starting your business, there are probably some basic functions that you need to stand up early on. These are likely going to be strategic objectives that need to be established, understood, and measured. John’s suggestion is to include those in your strategic plan in order to help you scale and grow. And this shouldn’t just be for the sake of standing it up, but for understanding what that objective means to you over the next five years.

Lean in, even if you’re feeling uncomfortable

If you’re new to strategic planning, John’s biggest piece of advice is to “lean in, even if you’re feeling uncomfortable, or even if you feel like you lack insight or trust about what your next three to five year goals should look like.”

Because, ultimately, you’ll have to drive the alignment not just with yourself or your executive team, but with anybody else that works with you. And that includes employees, customers, and partners.

Don’t plan around the “right now”

To make sure that Fearless’ strategic plan isn’t rooted in the “right now,” John says he and the executive team “make sure that any projects and activities they do can map back into their measure of success and into the actual high-level goal that they’ve set.”

By ensuring their projects and activities are grounded in their measures of success and high-level goal, Fearless is able to plan around the future. Rather than only focusing on what’s impacting the company right now.

Fearless also only “has three priorities for the year,” says John. “And then they have a series of projects broken down for the current trimester that map towards those priorities.”

From there, the Fearless executive team:

  1. Names the activity,
  2. Names the measure of success for that activity,
  3. Ensures the activity maps back into the larger goal that they’re trying to accomplish.

By spending the time on these steps, you’ll see very quickly if you’ve created a strategic plan that’s rooted in the right now, or if it has successfully accounted for the future of your company.

Ask questions

It’s easy to get “analysis paralysis,” as John says, when you “can see the things that need to happen, but can’t align all the pieces fast enough to get where you need to go.”

But what do you do when that happens? John suggests you ask a lot of questions.

Whether it’s to your executive team, management, or employees at any level of the company. Asking questions of many different people helps you build the case for context.

It’s also important to remember to “lean into the idea of being uncomfortable.” Sometimes you won’t know the answer, but you’ll still have to make a decision and live with the consequences. So, “be okay with knowing that you’ll potentially do something that people may not agree with.”

But when that happens, so long as you can measure your progress and outline what your leading and lagging indicators are, you’ll be able to see if you’re doing the right thing.

Start strategic planning early

As a founder and entrepreneur, you likely have many time constraints and real operational fires that need to be put out. And with so many other things taking up your time and energy, it can be easy to put off strategic planning. But Hutch Program Manager Stephanie Chin warns against this.

“It’s often easier to start building up these behaviors when your company is small,” she says. “Getting folks aligned on a strategic plan when you’re a handful of people, is much easier than trying to get 150 employees aligned to the priorities that you set.”

This means that you should start planning early. Even if you don’t think you have the time. In the end, you’ll be glad that you did so.

Solve patterns, not problems

“It’s the responsibility of you, as the owner of your company, to solve patterns, not problems,” says John. And strategic planning gives you the space to think about the patterns you’re seeing in your organization and helps you strategically solve them.

This work is hard, as it requires you to say “even if I see a fire, it’s okay for it to burn for a little bit because I need to solve another recurring problem in the organization.” But, while it might take you several years to change the pattern that you’ve identified, ultimately, solving that pattern will get you to your goals.

Identify weaknesses

When making a strategic plan, knowing the areas you want to improve is important. These will help you create priorities and goals during your planning sessions.

The first thing John does when he wants to identify weaknesses is “talk to a lot of people inside the company.” At Fearless, this looks like company-wide meetings held every other month, barnyard chats and Q&A sessions open to everyone at Fearless, and informal 1-1 meetings.

By taking the time to talk to many different people inside your organization, you’ll get the opportunity to understand how well your people are able to communicate and internalize the direction you’re moving in. And it’s also “a mechanism for employees to be able to push back.”

Plus, being able to hear from team members in candid, direct, and open ways gives you “greater context that can be layered on top of what you’re trying to do strategically.”

The second thing he does is tell the story of Fearless to a stranger. This creates an opportunity for dialogue, and it will allow you to see what you’re doing that makes sense and what resonates. In the end, this will either be a validation that you’re doing something right, or it will flag that you’ve majorly missed something.

Strategic planning is a framework, not a roadmap

Remember, strategic planning is a framework. This means that it’s meant to help guide you, but you’ll still need to put in the work to achieve your goals.

But, even inside this framework there’s still room for creativity. In fact, “you need to be creative and you need to take risks,” says John. You shouldn’t feel like this is “a mechanism to lock down your creativity.”

“Knowing who you are, what you want to accomplish, and being open to trying new things” will allow you to approach strategic planning in the way that works best for you.

Watch part of John’s office hour to hear his strategic planning tips.

How to develop a scalable and sustainable foundation for your business

It’s difficult for small businesses to create a strong and sustainable foundation on which they can grow. When new emergencies and exciting opportunities constantly pop up, it can feel like there’s not enough time to get your business where you want it to be.

That’s why we sat down with Felix Gilbert, CEO of XCell, Joey Price, CEO of Jumpstart: HR, and Koffi Harrison, CEO of UpLight. With their combined decades of founder experience, we knew that they would help illuminate some of the struggles entrepreneurs face when vision-casting for their businesses, and how strategic planning can alleviate those struggles.

The struggles they faced while building their businesses

There are countless struggles small business owners face that waste their already limited time. For Joey, Felix, and Koffi some of the issues they experienced were being reactive and thinking short-term, burning out from saying yes to everything, and putting in work without seeing any progress. All of these issues meant that, more often than not, they were working in their businesses, not on them.

Being reactive

For newer small businesses, it can be easier to create short-term strategies and focus on immediate wins, rather than long-term goals. And for Joey, this was definitely the case. “When I started out my small business, there was no such thing as planning ahead long-term,” he says. “It was more about thinking day-to-day.”

But, while a reactive response that focuses on the day-to-day can lead to wins, it can also often leave you wondering “now what?” If you’re failing to strategize long-term, you can get so focused on winning the contract that you’re unprepared for what to do once you have it.

Saying yes to everything

For Felix, building up his small business without a strategic planning framework in place meant he “literally felt like he was a hamster on a wheel.” He was so busy going after “every single government contract that existed,” that he ended up completely burnt out.

Without a clear understanding of your goals and what you’re working toward, it’s hard to know what to pursue. You’re more likely to say yes to every opportunity that comes your way. This can lead to wasted time and energy, when those are two things small business owners are already in short supply of.

Working hard without seeing any progress

One of the struggles Koffi highlighted was the amount of time and effort running a small business necessitates. She was “working non-stop for maybe 80 hours a week, but didn’t see any progress.” This lack of forward-momentum can be disheartening, especially when you’re pouring so much time into your business.

When you don’t have clear goals you’re working toward, it can be hard to know what to prioritize. This can then lead to you working long hours on projects that seem like a good idea, but don’t actually move your business forward.

The solution? Strategic planning!

So, how did Joey, Koffi, and Felix fix these issues? They created strategic plans for their businesses.

A strategic plan is designed to help you develop short-term goals to achieve your long-term outcomes. And at Hutch we dedicate an entire session to helping our cohorts create effective plans for their businesses. According to Felix, even years after graduating from the program, he still finds that “many of those goals that we had set in 2019, we’re still executing today.”

With strategic planning, you’ll be able to:

  • Move from being reactive to proactive,
  • Focus on what matters so you can get the best return on your time,
  • Actively work on your business, instead of just working in it.

If you want to learn more about creating a strategic plan, read our ultimate strategic planning playbook.

Become proactive, rather than reactive

By creating your own strategic planning framework, you’ll be able to break down your strategy and mission into digestible milestones that allow you to grow intentionally. This ability to be proactive is a key aspect of growing any business. After all, “you don’t want to be dragged into the future,” says Joey, “you want to create it.”

Know what to say no to

Strategic planning might seem like too much effort, but “by investing the time and creating a strategic plan for your company, you’re not only going to be more focused on the things that you do, but you’ll be more focused on what you say no to,” says Stephanie Chin, Hutch Program Manager.

Felix experienced this first-hand. Strategic planning “helped me scale beyond myself,” he says. And, by making sure “you’re actually running on the right path,” it gives you “the tools and resources you need while on that path.” These tools and resources will help you better align your projects and contracts with your goals and you’ll not only be better prepared to go after the projects you want, but you’ll also know what to say no to.

Make real progress in your business

Without a strategic plan, you’ll have a hard time keeping on track to meet your goals. But, by “staying focused and building where you are and building in alignment with your plan,” says Koffi, “you’ll see the fruits of your labor.”

According to Fearless COO John Foster, what proactive planning “allows companies to understand is when they get off track.” And this “ability to iterate, course correct, and ultimately understand where you are along the journey is equally as important as the destination itself.”

Strategic planning is worth the up-front investment in time

For small business owners, there often aren’t enough hours in the day to get everything done. And, when you’ve never used one before, it can feel like creating a strategic plan will require too much time for an unknown future reward.

But, while this work will require an upfront investment of time, it will save you time, stress, and headaches in the long run. Plus, by implementing strategic planning early in your company’s history you’ll build behaviors from the beginning that will allow you to grow your business effectively and use your time more efficiently.

Check out our video to hear Joey, Koffi, and Felix discuss their experiences with strategic planning.

The ultimate annual strategic planning playbook: How to set visionary priorities and make the most of your time every year.

When you’re a small business owner, making time for intentional growth and scaling is a real challenge. It’s easy to get caught in an endless cycle of putting out fires or responding to unexpected opportunities. When this happens, longer-term planning often falls by the wayside. It can feel impossible to plan for the future when more immediate needs are eating up all your time. 

But proactive planning is actually one of the best ways you can get time back

Annual strategy planning is just one part of the strategy planning framework we teach at Hutch, but it’s a key way that our entrepreneurs get out of the daily grind and make real forward progress. By making time for this kind of vision casting early on, you can set yourself up to see the growth needed to successfully scale. 

Looking for more time-saving tips? Check out our Time Management for CEOs Playbook. And for help focusing on what matters, read our Prioritization Playbook.

The annual strategic planning playbook

Our annual planning framework is designed to help you develop short-term goals to achieve your long-term outcomes. By connecting your day-to-day actions to your overarching vision, you’ll be able to grow intentionally in the ways you need to.


You’ll also be able to say no to those tempting distractions that threaten to derail you from your objectives. As Steve Jobs put it, “People think focus means saying yes to the thing you’ve got to focus on. But that’s not what it means at all. It means saying no to the hundred other good ideas that there are. You have to pick carefully.”

Illustration of a well blocked off calendar.
Illustration of an annual strategic planning roadmap.

Through the following plays, we’ll help you learn to say no by crafting a yearly roadmap that includes your priorities, goals, and strategies. Our annual strategic planning process will prompt you to identify the things that are essential and which will pull your focus away from your goals. It’ll also help you figure out how to balance all of this with your personal life.

Ready to get started?

The benefits of setting effective annual priorities. 

  • Improved return on time, giving you a laser focus on the things that will have the greatest impact on your business.
  • Better discipline and focus, enabling you to say no to anything that doesn’t align with your strategy.
  • Elimination of high-effort, low-impact tasks, allowing you to get out of the daily grind.
  • A more aligned and focused team, making delegating tasks easier and allowing you to shift from the primary doer to the visionary leader of your company. 

Play 1: Kick off your annual strategic planning by brainstorming all the things you might want to prioritize this year.

There are a million things you could focus on each year as a business. You might be looking to grow your team and scale your internal operations. Or you may feel like you need to work on systematizing your business development process. Revenue is a big priority, so you might need to focus on winning a few prime contracts in a key sector.


At this point, everything is fair game. Jot down anything you think you might need to prioritize this year to survive and thrive as a business. Don’t say “no” to anything yet. Just focus on generating as comprehensive a list of potential priorities as possible at this stage of the annual strategic planning process.

Illustration of an annual strategic planning brainstorming session.

Things to think about as you generate your priority list.

  • Are there specific customers you need to make ins with? 
  • Is there an industry you need to break into? 
  • Are there revenue targets you need to hit? 
  • Is there a capability you need to develop?
  • Are there shifts you’ll need to make to address changes in your customers’ behaviors?
  • Is there a weakness or threat you’ve identified as part of a SWOT analysis that you could eliminate? 
  • Do you have the internal processes in place to grow the way you need to? 
  • Is anything preventing you from delegating tasks, and if so, how might you remove those blockers? 
  • Do you need to expand your internal team to get where you need to go?

Play 2: Pick three priorities to focus on for the next 12 months.

At this point in your annual strategic planning, you’ll need to start whittling down the list you generated in the previous step. But first, take a minute to reflect on why you’re setting these priorities in the first place. 

Annual priorities allow you and your business to focus on the initiatives that will be most important for your forward movement. That’s why it’s so important to pick a limited number to focus on. It’s easy to be overly ambitious at this stage in the annual strategic planning process, which is why you should pick just three priorities for the year.


To help narrow down your list of priorities, we recommend hosting a sticky note session (either physically or virtually using a tool like Miro). You can do this on your own, but it’s useful to have partners — whether they’re peers, mentors, or business partners — to give you a fresh perspective. Then together, you can start combining and consolidating ideas.

Illustration of an annual strategic planning sticky note session.

Start by jotting your priorities down on sticky notes, then see if you can group them. Could any be combined? Are any redundant? When you’ve finished grouping your priorities, you can start to rank them. 

Use the following questions to help you test priorities and pick the three best ones.

  • Why is this priority critical? 
  • Will this priority enable you to take your business to the next level? 
  • Would achieving this priority put you closer to realizing your business’ vision? 

Once you’ve settled on your top priorities, write a brief description of them, along with an explanation of why they’re critical for your annual strategic planning.

Play 3: Pressure test your priorities (and revise as needed). 

Picking the right priorities is hard. It’s much easier to just choose a few that feel “good enough” and call it a day. But this can defeat the entire purpose of an annual planning framework. After all, priorities are only useful if they’re actually used. And this means you need very intentional and strategic priorities, as they’ll guide everything you do. 

So, how do you tell if you’ve picked the right priorities or if they still need some tweaking? You pressure test them.


It’s very hard to see the gaps in your own work, so it’ll be important to bring in fresh perspectives. This is even more important if you’ve been working on your own up until this point. If you have a peer, mentor, business partner, or even just a friend who’s willing to support you in your annual strategic planning process, ask them to help you evaluate your priorities.

Illustration of two people testing ideas with each other.

Put each of your priorities to the test by asking yourself the following questions. 

  • Is your priority clearly defined? You want each priority to be described so clearly that a stranger could read it and understand exactly what needs to be accomplished. 
  • Is the size of your priority appropriate for an annual goal? While there will always be problems that need to be addressed right away, your priorities should be bigger picture goals that can help your business take large steps forward. 
  • Does everything that you plan to focus on this year fit into these priorities? Your priorities are the north star of the annual strategic planning process, and they should influence everything you work on for the next 12 months. Because of that, you’ll want to make sure there aren’t any big tasks you plan to work on that don’t align with them. 

If you answered “no” to any of the questions above, don’t worry. Your priorities will almost never be perfect the first time around! Make some tweaks and repeat this step as needed until you’re a “yes” on all of the above prompts. 

Play 4: Set 2–3 goals for each priority.

At this stage in the annual strategic planning process, your priorities should be pretty solid. But how do you start to turn them into action? And how do you measure your progress towards them throughout the year? To start, you’ll need some goals. 

Aim to create 2–3 goals for each of your priorities. Your goals should be good proxies for the priority, and they should be easy to measure and time bound. 


For example, if your priority was to generate enough revenue to sustain your growth, one of your goals might be to book a certain dollar amount in revenue in the next calendar year. You might have another goal around the number of your existing contracts that are coming to a close this year that get renewed or extended.

Setting goals is a key point in annual strategic planning, as it’s where your more theoretical strategies start to become tangible action.

Illustration of setting goals.

Use the following questions to test each of your goals. 

  • Is your goal related to a priority?
  • Is your goal easily measurable?
  • Is your goal realistic in the given year?
  • Is your goal specific and concrete?

When deciding on your goals, make sure they’re broad enough in scope and that it’ll be easy to tell if you’ve accomplished them. Your goals should be big proxies you can track over time, like a certain number of contracts won or a percentage of projects completed on time and on budget, rather than lower level benchmarks. Those will come in the next step.

Play 5: Tie it all together into an operational plan. 

Now that you have your goals, you can start mapping out how you’ll achieve them. During this stage of the annual strategic planning process, you’ll start to get into the weeds of what exactly you’ll do and when. 

Taking one goal at a time, think through all the steps you’d need to take to achieve it. Then start attaching dates to each step. If you want to secure work with three new health agencies by the end of the year, for example, you might spend the first quarter doing business development research to find out which agencies most need your services. After coming up with a list of target agencies, you could start planning around their procurement schedules. After this, you may want to spend some time building strategic relationships before prepping for the proposals themselves.


No matter what your goals are, try to be as thorough as possible at this point. Good annual strategic planning requires both high-level visioning and in-the-weeds tactics for how you’ll get where you want to go. Your operational plans are how you bridge this gap, connecting your everyday actions to your long-term goals.

Illustration of an annual operational plan.

Questions to ask yourself to help develop your operational plan. 

  • What are all the actions you’ll need to take to meet each of your goals? 
  • What sequence would all of these actions have to happen in? 
  • What are the benchmarks and milestones that you’ll need to hit (and when) to ensure you’re on track? 

Once you’ve answered these questions, it can help to get an outside perspective. If you have a peer, mentor, or business partner you can ask for support, pressure test your plan with them to see if there are any gaps that need to be filled or revisions that need to be made.

Play 6: Add your personal life to your plan. 

At this point in the annual strategic planning process, you should have a solid understanding of your priorities, goals, actions, and benchmarks. But this is an ideal plan, and it assumes that you’re working on your business in a vacuum, with nothing else competing for your time. 

Unfortunately, that’s not how life works. 

Entrepreneurs are people first, and they have families and communities. Many work another job, on top of building their own business. If you don’t account for these realities, you’ll either try to do everything (and burn out fast) or some of your priorities will get sacrificed. 

That’s why the final step in the annual strategic planning process is adding in the rest of your life.


If you’ve got a big project due in February at your day job, you probably shouldn’t try to do a big business development push at the same time in your own business. Or if you’ve got a family vacation booked in June, you might want to make that a lighter work month all around. Whatever the reason, if you anticipate there being any constraints on your time, make sure you include it in your annual strategic planning and adjust your deadlines accordingly.

Illustration of a couple with a baby.

Things to think about as you generate your work + life plan. 

  • What does your capacity usually look like? If you tally up all the things you need to do outside of working on your business (including work on anything else, spending time with your family and friends, chores, errands, taking time for yourself, etc), how much time is left each week? It’s important to be realistic at this point; don’t try to fill every hour of every day. Instead, try to calculate the time you could put towards work while still balancing your other needs. That should be your baseline capacity. 
  • Are there periods where you know you’re going to have reduced capacity? While your baseline capacity is the normal state, there will be times when your capacity will be significantly reduced. As you’re working on this step of your annual strategic planning, try to account for periods when that might be the case as much as possible ahead of time. 

Once you have a sense of what kind of capacity you have to work on your business and when, you’ll be able to use this information to set more realistic goals and deadlines in your operational plan. 

If you do strategy planning right, you can achieve anything.


It can feel hard to make time to build out a planning framework, but it’s a critical tool in any entrepreneur’s toolkit. By working towards a set number of strategic priorities every year, you can hone your focus, cut the unnecessary, and free up your time. 

But learning how to do effective annual strategic planning can be deceptively challenging. After all, anyone can take a stab at following the above plays to create a plan. The hard part is figuring out if you’ve created the right plan.

Illustration of an entrepreneurial community of support.  

That’s why, at Hutch, we have dedicated strategic planning sessions. During them, our cohort companies create, workshop, and improve on various elements of their plans with advice from experts and from other entrepreneurs. With this built-in group of peers and mentors, our entrepreneurs can bounce ideas off each other and get advice from people with expertise in their specific problem areas.

 By getting early feedback from others as they craft their plans, our members are able to pressure test and hone their ideas early on in the process. And this can save them from issues and rework later on, allowing them to identify (and sidestep) any potential pitfalls before they start running. 

Want to learn more about annual strategic planning

Do you have questions about how to plan out your yearly strategy? Sign up for our weekly newsletter. We are sharing tips and education from our cohort classes, and subscribers get first access to free webinars.

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Learn to succeed in government contracting-virtual bootcamp

The federal government spends more than $500 billion annually on government contracting. When you factor in state and local government contracts, the industry is growing by leaps and bounds. But how do you get your foot in the door and establish yourself at the local, state and federal level?

Hutch and Drake Strategy & Associates are offering a 7-week virtual bootcamp to teach you the strategies to get top government executives interested in meeting with you and win government contracts.

Things to know:

  • The session runs June 6th through July 25th
  • Virtual classes every Tuesday 12:30-1:30pm EST
    • There is no class the week of July 4th
  • $895 total cost for all sessions and materials (Check out our LinkedIn for a coupon code for $200 off)
  • Registration closes May 22nd

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