A Talk With Eileen Kent – Insights for Small Businesses in Government Contracting

May 17, 2024

Venturing into government contracting may appear daunting, yet with a well-crafted plan and expert guidance, you can embark on this journey and drive revenue. Recently, we engaged in a conversation with Eileen Kent, a seasoned Federal Sales expert known for illuminating the path for numerous businesses entering the realm of government contracting. Eileen shared her invaluable insights on the essential knowledge small enterprises should possess when navigating the intricacies of selling to the government in 2024. Here’s what she had to say.

Eileen, as we course through 2024, what message would you like to give small businesses eager to enter the government contracting space this year?

Eileen: The most important thing a small business must do first in this marketplace is to focus.

  • Focus on a specialty product or service you’re great at delivering already to the commercial marketplace. Lead with your capabilities and close with your small business set aside.
  • Focus on the agency or agencies who buy what you sell.
  • Focus on building strong relationships within those agencies, not only with the small business officer and the contracting officers, but also the program and project managers who need what you sell.
  • Focus on the program and project managers’ pain and make it your mission to solve their challenges. Entering this market with “a mission to help solve problems” instead of “a mission to make millions in days” will get you everywhere.
  • Focus on knowing your competition and potentially turning some of the competition into your “compe-ti-mates” or teaming partners.
  • Focus on only writing winning proposals for the agencies and the people you know within them. Don’t surf the public bid sites all day looking for what to bid, but look for the opportunities you already knew were coming down the pipeline and who your potential customers are. This focus can be easier when you’ve done all the above and created a solid bid/no-bid decision process.
    Put this on the office fridge: “Only Write Winners!”

If you don’t know the answers to any of the above, get training and get someone to perform a competitive analysis for you to determine exactly who buys what you sell from whom and how. Then, build a federal sales action plan around those people within those agencies and start executing the plan by building relationships.

Thanks for the insightful answer. Another question: when selecting the right buyers, would you suggest that small businesses focus their efforts on a few selected agencies, or is it beneficial to cast a wider net by approaching multiple agencies?

Eileen: It depends on your business, but yes, focusing on a handful of agencies (five or less) is the best way to start. But note that some agencies have dozens of locations, so you may also have to drill down even further and focus on the region that decides what you sell or focus on only selling in your backyard.

For example, if you were in construction, GSA’s Public Building Service is the construction manager, facility manager, and real estate office for all the federal buildings and courthouses across the country. If you’re a small construction company in the Midwest, it may make sense to focus only on Regions 4 and 5 of PBS because they’re in your backyard. But other small construction companies like you may already have five-year construction repair and alteration contracts working with those regions, so your approach may be to team up with them first.

If you’re an IT company selling health records, sure, the VA is a great focus—but there are thousands of locations across the US. However, there is a hotspot location in the country that manages the contracts for Health IT records. It would take research to find out who inside that location is to talk to and who their current vendors are to become competitors with—but that information is available. Once you know who and where you can focus all your sales efforts on that hotspot.

However, if you’re a medical supply company, you may need to get into every Medical Center at the VA and talk to the key decision maker – location by location – to get them to switch to your products and services. But what if you need to have a contract vehicle or to be a Service Disabled Veteran to even talk to them? That’s when you need to know exactly who the Medical Center is buying from, and, again, go make friends with the competitors and team up with them.

Everyone new to this industry thinks everything is posted on System for Award Management, but it isn’t. Many deals are completely “under the radar” through current contract vehicles, single-award blanket purchase agreements, set-asides, and more. Many smalls are missing the point that they must do their homework first to understand who buys what they sell, how they buy it, and from whom they buy it – so they can follow that specific path. The data is out there; you just need someone to interpret it for you and build an action plan. Then, the idea is to capture the opportunity months or years before it’s competed on SAM or GSA, or better yet, to get the customer to set it aside for small or sole source it to you.

That makes sense. Many of our readers are aspiring government contractors with no past performance in the federal market. What advice would you give them for effectively leveraging their commercial success and the expertise of their key personnel to secure government contracts?

Eileen: If you’re entering this market, the feds like to work with companies who have past performance with them. So, working with primes as a sub is one way to get some past performance on the books. But if you have some name-brand commercial clients or clients the feds may recognize, they may “open the door” in the past performance requirements in the bid to allow you to put in your commercial past performance. But that takes – a relationship.

For example, I landed my first deal with DHS when they opened their very first offices. I was recommended to the HQ of DHS by another agency who was very – unhappy – with their current vendor (my competitor). The DHS customer asked me, “Do you have any past performance with the federal government?” I said, “Not with the federal government, but we’ve been in business 25 years, and we worked with XYZ Prime recently (and I described a project that had been in the national news with that Prime).” The customer told me to put that past performance into my proposal when he posted the bid. In the RFQ bid document, they put, “You must have past performance with this agency or similar size and scope with a Name Brand Prime.” You see? He opened the door enough for me to put in that past performance with the Name Brand Prime we discussed – and I won.

So, the bottom line is this: They’ll let you use Commercial Past Performance when they’ve actually spoken with you, realize your capabilities, and want you, and they open up the past performance requirements in the bid for commercial past performance, too. If they prefer an incumbent contractor or contractors they know have federal experience, they’ll put in, “You must have past performance with the federal government or this agency,” and you’re out of luck. You can’t bid – OR – you team with one of those known contractors.

Speaking of scale, contract vehicles can be a significant gateway to recurring government business. Should small businesses prioritize these, or is it better to aim for smaller, direct opportunities initially?

Eileen: I hate to say it, but it depends on what you sell.

Some products under $10k can easily be purchased under the “micropurchase threshold” and sole-sourced a contract with you if they want to buy from you directly without a contract vehicle. Also, small businesses can get three quick quotes under the Simplified Acquisition Procedure.

But if they repeatedly buy from you and their orders are all $9,999.00, they’re going to get called out on it by management, so they may need a contract vehicle to show they shopped and that the prices are considered “fair and reasonable.” They may also need a contract vehicle to create a “BPA-Blanket Purchase Agreement” so they can order from you over and over again. Having a Contract Vehicle like a GSA Schedule makes it really easy for the buyers to create BPAs.

Contract vehicles are very popular because they make it easy for buyers to award projects quickly and quietly, well within the rules. It also limits the exposure to the public and the number of bids they receive. Plus, the agencies with contract vehicles: GSA MAS, GSA GWACs, NASA SEWP, NAVY SeaportNXG, HHS CIOSP3(and 4), and so on….These agencies have done a great job vetting the companies, their backgrounds, capabilities, and pricing. The FAR allows the agencies to use these contract vehicles to place orders under $25k on GSA Advantage (their online shopping site) or to get three written bids when the deal is over $25k. It takes 269 days to start a project awarded on SAM, while it takes 14 days on average when it’s completed on the GSA Schedule. So, vendors with GSA schedules, are making the contracting officers’ jobs easier for the agencies to purchase quickly and within the rules.

However, word of caution – many smalls are convinced they need these contract vehicles to succeed, and I highly recommend smalls make sure – through research in past contracting data – this is true. Time and time again, I see companies get on the GSA Schedule, which costs $10k-25k, and it costs a year to get on it, only to find out no one uses GSA to buy what they sell. I have so many examples of competitive analyses I’ve done for companies with a GSA Schedule – showing very little going through the GSA Schedule in their area of expertise. 50% of the vendors are on GSA at $0 sales. Why? Because the companies sit and wait for the orders and never market and sell themselves, or the federal buyers don’t use GSA to buy what they sell. Do your homework BEFORE you invest in a contract vehicle or hire someone to do it for you. When you get that contract vehicle, don’t sit and wait for the orders; go get your customers and show them how to buy from you on that contract vehicle.

Eileen, many businesses wonder if relationship-building with agencies carries more weight or actual proposals that they submit. What is your take on the importance of proposals as a deciding factor for awards?

Eileen: You can’t win anything without responding to an actual bid but won’t win much without relationships.

Will you get lucky and win a bluebird deal once in a while? Yes. But I highly recommend small businesses perform a bid/no bid decision prior to responding to any bids because they’re time-consuming and costly—especially if you’re paying a proposal writer to put it all together for you.

What do you ask yourself:

  • Who do I know inside the agency?
  • Who knows us inside the agency?
  • Did anyone recommend us for this opportunity?
  • Did we do a capabilities briefing for this organization?
  • Do we know their pain?
  • Do we know their perceived solution?
  • Who is the incumbent?
  • Who are the other “usual suspects” (competitors)?
  • What is the actual story behind this bid?
  • What is the Win Theme? (Do we have what they told us they wanted, and are we the only ones with it?)
  • Can we deliver on time, everytime, within budget – perfectly?
  • Do we fit the set-aside?
  • Do we have the contract vehicle?
  • What is the budget?
  • How do we price?
  • Will we make money? Let me say this once again – Will we make money?
  • When is it due?
  • How many of our answers above are “wishful thinking?”

I’m not saying NOT to bid, but be selective. Proposals are not easy to write (even with AI Proposal Software, you need a person to make sure they’re perfect and your pricing is right).

Your chances are much higher if you are known at that agency.

It’s a relationship.

With the economic outlook appearing to stabilize after last year’s recessionary trends, what strategies should government contractors implement now to best position themselves for success in this evolving economic climate?

Eileen: Every business/area of expertise is different, but here’s a basic formula:

  • Get training in Federal Sales, Proposal Writing, GSA Schedule Contracting/Management, Pricing, and Back Office Management – or hire experts to help you.
  • Perform competitive analysis – or have someone really good do it for you
  • Build a focused Federal Sales Action Plan – or have someone really good build it for you
  • Build a consistent and strong marketing program via Social Media, specifically LinkedIn – where you can find 2M+ federal customers. Post great articles, whitepapers, and videos for professional exposure
  • Execute the federal sales plan religiously like your business depends on it (because it does); that means hiring salespeople
  • Write only winning proposals that you price right and make money – you’re not a “non-profit.”
  • Deliver perfectly, on time, and within budget; be compliant and follow the rules
  • Find great teaming partners
  • Get great reviews and references from your clients – work hard to get “Exceptional” ratings
  • Have patience, be persistent, and persevere no matter what

Rinse and Repeat


Eileen’s advice sheds light on the strategic approaches small businesses can adopt to enhance their prospects in government contracting. Her emphasis on understanding the importance of strategic selection of opportunities could be particularly beneficial for newcomers in the field. We thank Eileen for sharing her expertise with us and for her continued support in helping small businesses navigate the often intricate world of government contracting.

Eileen Kent, President of Custom Keynotes, LLC, is known as the “Federal Sales Guide” who Builds Industry Intel & Customized Winning Federal Sales Action Plans for Contractors through her ‘Three-Step Program.’ Over 10,000 people and 350 companies have been trained since 2002.

iQuasar’s Government Contracting Consulting Team helps many budding government contractors who want to kickstart their government contracting business by providing them with necessary guidance, assessment, registration, and other support related to required processes. We have experience supporting multiple new government contractors to start and grow their businesses. If you are a new business wanting to foray into this space, feel free to contact us today. Stay tuned for more insights from industry experts in our upcoming posts.


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