Matthew O'Connell

Most GovCon companies don't lose on capability. They lose on timing. The pattern is almost always the same. Win the contract, then invest in the product. Get the product stable, then start marketing. Build the pipeline, then figure out what to sell. It feels disciplined. It's actually just slow. By the time each track is ready to hand off to the next, the opportunity has already shaped itself around someone else. The incumbent renewed. The budget got reprogrammed. The program office stopped returning calls. Here's what I've seen work instead. BD pursuing live opportunities while engineering is hardening the platform. Marketing building market presence and credibility before there's a contract to point to. Sales developing relationships in programs you haven't won yet — and may not win for 18 months. These tracks don't wait for each other. They inform each other. The objection I hear most from technical founders is "we don't have the resources to run all of this at once." That's a real constraint. But serializing doesn't conserve resources. It just redistributes the risk onto your timeline and in GovCon, timeline is the one thing you can't recover. At that point, sequential GTM isn't a strategy. It's just a slower way to watch someone else win. What's the track most technical founders underinvest in first, and why is it almost always marketing?

9

Most defense contractors think they have time. They don't. November 2026 sounds far away until you realize the average SMB takes 18-24 months to reach CMMC Level 2 compliance. Do the math. The window is closing fast. Here's what I keep seeing: companies doing real work for the DoD — good companies, talented people — running their entire security posture on spreadsheets, good intentions, and hope. No documented policies. No continuous monitoring. No audit trail. Just a prayer that nobody looks too close. 86% of defense-sector SMBs aren't ready for CMMC 2.0. That's not a statistic I read somewhere. That's what I see when we actually get inside these organizations. The traditional answer has been to hire a security team. We're talking $400K-$500K per year in fully-loaded labor costs before you buy a single tool. For a 50-person manufacturer, that's often not survivable. We built SecureWatch because there had to be a better path. A platform that handles continuous compliance monitoring, documentation, audit readiness, and gap analysis — for $799 a month. Not because we cut corners. Because we engineered out the inefficiency. The contractors who win DoD work in 2027 and beyond will be the ones who treated compliance as a competitive advantage, not a last-minute checkbox. The ones who wait will either scramble at enormous cost or lose their contracts entirely. If you're a defense contractor and you haven't had an honest conversation about where you actually stand on CMMC readiness — what's stopping you from having that conversation this week?

1

Most Popular Question From Government Contractors. How can I use AI to find bids on SAM.gov? I share practical experiments to run with a tool they already use. The questions I ask them are: 1. What does the Intelligent Pipeline Assistant need to do? 2. Can you walk me through your current search and scoring process? 3. How often do you do it? 4. What is your website URL, and do you have your capability statement handy? 5. Do you have a capture strategy? Then, based on that answer, here is one method I show: 1. Open ChatGPT 2. Set up the Claude Project (If they have a Plus or Pro account) 3. Enable Agent Mode 4. Customize this shortened version of the prompt "You are a government contracting research agent. Your mission: Find and analyze active federal contracting opportunities on SAM.GOV that match specific criteria in the technology sector (software development, IT infrastructure, cybersecurity, data analytics/AI/ML)." Add your: -Contract value range -Set-aside preferences (small business, veteran-owned, etc.) -Period of performance -Geographic focus" For each opportunity, ask ChatGPT to provide: -Opportunity overview (title, agency, value, deadline) -Technical requirements -Business intelligence (competition, past awards, procurement patterns) -Strategic recommendations (bid/no-bid, partners, gaps, proposal timeline) I have the person incorporate the answers to the questions I asked. This zeros in on bids that fit. You’ve set up a structured and repeatable intelligent digital employee pipeline. You can modify this for other public data sources to find leads. It reveals hidden trends and connections that you miss in manual searches. You can expand with more data and insights. Set up a Scheduled Task to get notifications from ChatGPT based on the results. What did we do differently? We approached the questioner's problem strategically with AI's assistance. That was the key. If you want the detailed prompt, let me know. I’ll be presenting a session on finding SAM.GOV opportunities faster with digital employees and THINK at the Central Maryland Chamber AI & Tech Conference on Tuesday.

6

1 Comment

At OnFrontiers, I get a front-row seat to how contractors navigate today's uncertain federal marketplace. Large DOD contractors? They seem to be absorbing uncertainty through volume. But smaller contractors face a different reality. When 1 of your 4 programs gets cancelled, that's 25% of your pipeline gone. Some are asking: "Why bother with capture? Let's just pump out AI proposals and see what sticks." This seems like a dangerous trap. A capture leader recently shared a framework that cuts through the noise. To win, answer four questions: 1) What's the customer's real problem? Beyond the RFI—what keeps them up at night 2) What's our differentiated approach? How we solve this uniquely 3) What specific benefits will they see? Tangible outcomes, not features 4) Where's our proof? Concrete examples of similar results. It is obvious that teams that nail these will consistently outperform, but you can't answer them without real capture. So how do you invest in capture when cancellations are at an all-time high? The answer: Agile Capture We're piloting this with our users, built on three principles: 1) Cast a wider net with sharper focus. Track opportunities 6-9 months out instead of 3-6. The old 10:1 review-to-submit ratio? Now it's 20:1. Build a pipeline that can absorb cancellations. 2) Use AI intelligently for early research. At OnFrontiers, we combine AI with expert intelligence for dynamic win plans. This isn't replacing human judgment—it's getting to critical questions faster. 3) Stage investments by confidence level. Early stage? Just expert calls and competitive intel. As confidence grows, add pricing analysis and teammate discussions. Don't over-invest in opportunities that might disappear. 4) Stay ready to pivot. When that recompete becomes a small business set-aside, agility matters. Successful contractors have playbooks for common pivots. Capture managers who juggled 3-5 opportunities may need to now manage 10+. It's a fundamental shift. How are you adapting your strategies? What's working for your team?" #GovCon #FederalContracting #BusinessDevelopment #DefenseIndustry #Procurement

36

So… I’ve been diving into the Practitioner Album’s draft of the FAR Part 6 Competition Requirements Rewrite, and let me just say: If you’re a small business in federal contracting… this ain’t great news. We haven’t seen the full blockbuster rewrite of FAR Part 19 (Small Business Programs) yet, but judging by this sneak peek of Part 6… let’s just say the small business community is getting some serious foreshadowing vibes and not the good kind. What’s Missing? (Besides Logic… 😅) No mention of the Rule of Two..that critical policy that requires set-asides for small businesses when at least two qualified small businesses can do the job at a fair price. No references to our small business socioeconomic programs like 8(a), HUBZone, WOSB, or SDVOSB for set-aside or sole source awards. And here’s the kicker….Contracting Officers would now “retain discretion” on whether to set aside work for small businesses at all. Discretion. Not requirement. Just… discretion. If you’ve been in this game long enough, you already know. This isn’t just a technical rewrite. It’s a fundamental shift that could lead to ; Fewer small business set-asides; Fewer sole source opportunities and Less predictable access to federal work. And let’s be real… most small businesses don’t have the luxury of sitting around hoping a CO chooses to give them a shot. We built businesses on the backbone of the Rule of Two and the protections inside FAR Part 19. Taking those out of Part 6 (without knowing what’s coming next in Part 19) feels like we’re being pushed out of the room before the conversation even starts. So… What Do We Do? —>Stay informed. —>Start paying attention to these draft changes (yes, even the boring ones… I know, trust me, I know). —>Be ready to submit public comments when the time comes. If you’re a BD lead or proposal manager—start strengthening your past performance and technical narratives now. And most importantly… Don’t stay quiet about this. Because policy shifts like this happen when small businesses are too busy chasing contracts to notice the rulebook getting rewritten. If you want help understanding how this could affect your upcoming bids, hit me up. We’re watching this closely… and we’re not going to let small businesses get pushed to the sidelines without a fight. Stay tuned….. #govcon

17

3 Comments

3 steps to navigate the DoD’s hidden power structures There is no front door to the Department of Defense. Only a maze of stakeholders who don’t speak your language If you’re a startup trying to break into defense, you already know the feeling: • You demo • They’re impressed • Then… nothing That’s because most founders approach the DoD like a single buyer. But Giles W. - retired Marine and former AWS mission lead - says federal traction happens when you solve for three separate power centers at once. Here’s how he breaks it down for early-stage teams: __________________________ Step #1: Earn trust at the edge This is the warfighter (the end-user who actually needs your tech) They’re the ones facing the problem you solve. But showing up with a sharp demo isn’t enough. You have to: • Solve an actual operational pain • Prove usability in the field • Get them to advocate up the chain Without their support, your tech’s just another line in a white paper. __________________________ Step # 2: Speak procurement to the PM Program Managers are the system owners. They hold the purse strings and care about: • Compliance • Integration • Risk Giles calls this the most overlooked gatekeeper. Founders win by mapping capabilities directly to what the PM’s protecting—not just what the warfighter wants. Your job is to make their job easier. __________________________ Step # 3: Align to a senior leader’s mission (without wasting their time) Senior leaders aren’t blocking you, they’re buried. “Clobbered with time,” as Giles puts it. You need to: • Show clear strategic fit • Help them visualize outcomes • Never over-explain This is where mission relevance, timing, and optics meet. __________________________ Most founders sell to the DoD like it’s one person. It’s not. It’s a three-headed buyer. And you only break in when you earn the trust of all three. That’s how Giles now helps pre-Series A companies survive federal. This is just the map outline. Giles walks you through the terrain. Listen to the full episode of The Amplified CEO https://lnkd.in/ea2sS8w5

56

8 Comments

Trying to meet all 1,600 vendors at DSEI is like trying to clear a minefield with a teaspoon — technically possible, but you’re not coming out in one piece! But even spending time with a fraction of them sharpens the knowledge base. Every chat, whether it’s about fire retardant paint on main battle tanks next-gen armour, cyber resilience, video streaming or “that bit of kit you never knew you needed,” adds a new layer of perspective. That’s the strength of DSEI — it’s not just the kit on display, it’s the conversations that move capability forward. Military, industry, innovators: everyone’s trading insights, war stories, and on our stand - chocolate bars! Sometimes it only takes a handful of those encounters to spark big opportunities. The real challenge? Keeping the notebook legible after day one! #DSEI2025 #Defence #Innovation #MilitaryNetworking #CrossDomain #defense #military Neroshield HMG Paints Ltd CBRNE & CT ATLANTIC BRIDGE (CAB) Iris Technology Guild Associates, Inc #networking LiveU Public Safety

22

2 Comments