Jason Bennett’s Post

Take the pain: Why you’re not ready to outsource marketing/sales. In my last startup, we had customers day 1 (M&A spinoff)  We put in the work and launched an ‘industry’s first’ SaaS To bump growth, I chose to outsource marketing and sales. Big, huge mistake!  Here’s why: 1\ No one understood the product or customers better than me/us.  2\ Our current customer’s weren’t [necessarily] our next customers.. .so we did not have market fit thus no agency or contractor could “market” us into growth.  3\ Without knowing 𝘦𝘹𝘢𝘤𝘵𝘭𝘺 who our ICP was, our sales/marketing efforts were simply guesswork.  Unfortunately, the results were: → High acquisition costs.   → Poorly qualified leads.   → Sales cycles that drag on forever (or never); Time, money, resources, ouch! If you’re a technical founder, here’s a harsh reality 🥊:  → You need to lock in your niche and validate product-market fit 𝘣𝘦𝘧𝘰𝘳𝘦 throwing money at external help. → Only you can iterate fast enough. → Only you can get deep in the trenches with your ideal customers to understand what resonates. Once you know: → Who your perfect customer is,   → Why they’re buying,   → And how your product solves a specific pain point,  𝘛𝘩𝘦𝘯 it’s time to scale up with marketing and sales resources. Painful?  Not if you have the right mindset and discipline. Don’t outsource the heart of your business too early. Get clear on your ICP. Nail product-market fit. Once you’ve got that dialed in, the marketing and sales strategies will follow. It pays off, I promise you. Hope this helps.   ____________________________   I help technical founders be CEOs and win.

Scale ≠ More Chaos Most founders think scaling means doing more. More sales. More customers. More chaos. 🥊  Wrong. Scaling isn’t about throwing more into the mix. It’s about simplifying the complex. Here’s the real formula: → Scale = fewer moving parts automated processes empowered teams.   → It’s about doing more with less—less chaos, less friction, less manual effort. Your business doesn’t need more work. It needs systems that work for you, not against you. Think about this: ⁉ If your team can’t handle the business today, how will they handle it when you 3x your customer base? You don’t scale by adding complexity. You scale by streamlining. 💡 Your systems should grow with you, not slow you down. 💡 Focus on fewer, better processes. Get your team running like clockwork. Then, scaling will become the natural outcome—not a nightmare. Hope this helps. _________________________ I help technical founders be CEOs and win. 

You’re not scaling because you’re trying too hard… To grow your business you need salable operations. But most SaaS startups stall because they’re stuck with outdated processes that don’t grow with them. Here’s what typically happens:  1\ You bring on new customers faster than your systems can handle.   2\ Your team spends more time fixing problems than driving growth.   3\ You lose sight of long-term strategy because you’re focused on the day-to-day.  🥊  Sound familiar? The key to breaking out of this cycle is simple:  → Streamline your core operations.   → Automate tasks that don’t require human decision-making.   → Get your team aligned on clear, measurable goals. Remember: Scaling isn’t about doing more. It’s about doing more with less, at speed.  Efficient operations free up your time, your team’s focus, and create space for growth. If your business is slowing down, it’s time to look at the engine running it. Fix the inefficiencies before they become full-blown bottlenecks. Hope this helps. _________________________ I help technical founders be CEOs and win.

The real barrier to scaling could be you If you’re a technical founder stuck at $1M ARR and can't seem to break through… chances are it's not your product holding you back. It’s your processes. Most founders I work with are buried in the day-to-day because they’ve built a business that can’t scale without them. 🥊 Hard truth: → You can’t scale what you don’t systematize.   → Growth won’t happen if your team is waiting on you for every decision.   → Your business processes either work for you or they work against you. Ask yourself:  ⁉  Are your operations lean and automated, or do you spend your time putting out fires?   ⁉   Do you have clear, repeatable workflows or does your team improvise on the fly? The reality is, scaling isn’t just about adding more sales or closing more deals. It’s about building a business that runs without you being involved in every little thing. If you want 3x growth, it starts with you stepping back and letting systems do the heavy lifting. Optimize. Delegate. Then, scale. Hope this helps. _________________________ I help technical founders be CEOs and win.

I’ve consistently ramped my clients’ time to revenue by >300% 99% of them fall into 2 big traps—endless planning and inertia—mistakes that keep them going nowhere Here's how to quickly fix that (so you can turnaround and ramp revenues): 1/ Positioning:  ↳  You get 1 hour: 5 problems, 5 solutions, 10 USPs, 3 hyper-specific outcomes 2/ Channels ↳  What are they?  What’s unique about each? 3/ Scorecard: Metrics & KPIs ↳  What’s winning look like?  Who’s accountable?  Daily huddles. 4/ Experiments: ↳  Simple, effective framework.  Time bound.   Stick to the rules. 5/ Iteration cycles ↳  How, what, when.  Stick to it.  Make a decision, move on. Listen, execute, learn → Keep going. Questions? ______________________ I help technical founders get out of sales and boost investor confidence.

What my most successful clients have in common might surprise you: They didn’t set out in life to run a tech startup. Hell, neither did I… way back when. Does this sound familiar: → You had a secure corporate job (cushy comfort) → Made big money (knowing way less than the boss) → You saw a big problem and knew you could solve it → You caught the bug and worked up the courage…. → Now you’re leading your first tech startup. You’re an expert at what you do. You sort of mashed your way through getting to this point. You leveraged your network to get customers. Soared past the coveted $1M ARR But now… ❌ Referral network is used up ❌ No repeatable way to get to new business ❌ Stakeholder and investor confidence is slipping ❌ You tried to outsource growth but that ended badly (again, and again) You no longer or very rarely go on holiday or date nights. You are a problem solver and growth, marketing, sales, networking isn’t your thing You can’t lose the accounts you do have (but not sure about retention processes) You’d rather be innovating than dealing with this stuff. But, here you are. Basically, you’re stuck. Weeks, months. years… stuck 🕰️ Bad hires, balancing profitability, borrowing more money Desperately building features and throwing them at new markets It’s like Groundhog Day over and over and over again. Here’s the deal: My clients focus only on what drives value. 💡 Set clear, achievable yet aggressive goals.  💡 Get everyone on the same page, and excited again.  💡 Use proven frameworks, processes, and optimization tactics,  💡 Hold themselves and others accountable  💡 Make fast decisions and move on  💡 My clients learn to delegate, communicate, and lead 🚀 And know that I help them: → Attract their perfect customer → Close more deals faster, at scale → Implement lean, scalable processes → Progressively have more time to do what they love. It’s not rocket science It’s expertise, no bullshit, and empathy because I’ve been there, and Backed by 5 years consulting in big tech Fortune 50   15 years business building in B2B SaaS/enterprise tech with 2 exits. When you’ve had your ass kicked enough and are ready to get serious about putting your mark on the world, Your legacy. Let’s talk. Or, keep doing what you’re doing and see how that goes. Then, when you’re ready to 3x growth in one year…. ------------------ I help technical founders build the business their product deserves.

Not having a growth system is probably why you’re not, well, growing. I meet with 00s of technical founders every year and I’m always asked, “What is a growth system?” To answer that, let’s uncover growth system Growth is quit possibly the most overused yet misunderstood buzzword in startup land, period. For clarity, growth is not equal: ≠ Scale ≠ Revenue ≠ Digital marketing ≠ Sales ≠ And more… Growth is when you have the bits and pieces of your business model aligned such that things don’t break, like: 〰️ Slow onboarding 〰️ Longer than normal sales cycles 〰️ Slow onboarding 〰️ Systems outages 〰️ Churn And so on…. Now, “system” To keep it simple, we’ll define “system” as 💡 unified processes aligned and measured to meet a goal or outcome.  Enter a Growth System: →  Sales engine; →  Business processes; →  Leadership; →  Cash flow. In a nutshell, this is your growth system. This doesn't have to be a huge deal.  But you must be deliberate and optimize, optimize, optimize. Get all those birds humming the same tune. Voila! 🐥 Next we’ll talk scale. Hope this helps. __________________________________ I help technical founders attract the perfect customer and close more deals at scale while having more time to do what they love.

7 things to fix why you’re not ready to outsource growth About a year ago I turned down a lucrative fractional CRO role. My then prospective client is a technical genius, built a great product, but stuck at around $3M ARR for well over 2 years. I was asked to build a winning program and team. I decided it wasn’t a fit after asking a few pointed questions: → Who is your perfect customer? → What’s your unique value prop? → What’s the overall goal I’ll be measured on? I knew it was a no-go when he stumbled on question 1… Hard truth:  You simply cannot outsource your growth without clarity on the basics. Here are 7 must-haves before ever hiring for growth 1/ Market/Product Fit ↳  Yup, market comes before product when you know who your perfect customer is and know that you solving their problem(s)? Otherwise traction is hard. 2/ Documented Personae ↳  Create and continue to update a ‘perfect customer profile’ doc.  Their pain points, decision-making process, and where to find them. 3/ Established value proposition ↳   Articulate a 𝗰𝗹𝗲𝗮𝗿 𝘃𝗮𝗹𝘂𝗲 𝗽𝗿𝗼𝗽𝗼𝘀𝗶𝘁𝗶𝗼𝗻 that sets your product apart from competitors. Any growth hire must know this, the benefits, and unique selling points. 4/ Metrics and KPIs ↳  When you do hire, set the tone out of the gate by having clearly defined ‘key metrics’ and KPIs their success will be gauged on.  Think about it. 5/ Sales process outline ↳  Even if it’s written on a cocktail napkin, there should be a basic sales process in place. Inbound, outbound, or both? Frameworks you’ve used both good and bad. 6/ Budget and resource allocation Money and time are most valuable to you… know what you’re willing to fork over and when to stop.  This includes your new hires and existing resources including you. 7/ Always begin at the end ↳  Set specific, measurable goals  for what you want the consultant or agency to achieve. Whether it’s increasing leads, improving conversion rates, or building brand awareness, having clear expectations drives success. Chances are you already have most of this knowledge because you’ve been at this for awhile.  Find what’s missing and fix it before spending a dime and time on outsourcing.  It’s the game-changer.  Promise. Hope this helps. __________________________________ I help technical founders attract the perfect customer and close more deals at scale while having more time to do what they love.

More customers won't get you funded. But this will... Technical founders often tell me, “I just need customers so I can get funded.” Unfortunately, more customers doesn’t cut it, there’s more to this game. The first time I raised $1M… Back in the day, I was building Unna, the ‘there when you can’t be’  AgeTech for family caregivers. I had growing users, plenty of bells, whistles, and a helluva brand.  With my connections, salesmanship, and charm, I thought I would close my $1M seed in 8 weeks. Easy peazy!  Nope.  Took 3x longer because I had so much to learn about building and raising. 🥊 Hard truth:  Investors aren't throwing money at cool tech or because you can revenue; or Simply because you have landed a few more customers. It’s about the complete package. 4 things you should know before raising capital: 𝟭/ 𝗦𝗰𝗮𝗹𝗮𝗯𝗹𝗲 𝗖𝘂𝘀𝘁𝗼𝗺𝗲𝗿 𝗔𝗰𝗾𝘂𝗶𝘀𝗶𝘁𝗶𝗼𝗻: ↳ Forget "hockey stick" projections. Demonstrate a repeatable, scalable customer acquisition engine. Prove you can consistently attain/retain customers. 𝟮/ 𝗠𝗲𝘁𝗿𝗶𝗰𝘀 𝗧𝗵𝗮𝘁 𝗠𝗮𝘁𝘁𝗲𝗿: ↳ It's not growth; it's profitable growth. Keep CAC in check and at least 4:1 CLV:CAC.  Make sure NDR is above 110% - Show your customers stick around and spend more over time. 𝟯/ 𝗦𝘁𝗿𝗼𝗻𝗴 𝗟𝗲𝗮𝗱𝗲𝗿𝘀𝗵𝗶𝗽 𝗧𝗲𝗮𝗺 ↳ Investors bet on people as much, or more, as products. Showcase proven track record, deep industry expertise, and your ability to execute, adapt, and navigate the challenges. 𝟰/ 𝗩𝗶𝘀𝗶𝗼𝗻: ↳ This is where you, the technical founder, truly shine. Articulate a clear and compelling vision for the future of your company. Show passion, mastery of the market, and your ability to inspire and lead a high-performing team. 𝗔𝗻𝗱, 𝘁𝗼 𝗿𝗲𝗮𝗹𝗹𝘆 𝗻𝗮𝗶𝗹 𝗶𝘁: → Demonstrate a large and growing market with a clear path to capturing significant market share. → Show consistent growth in key metrics, proving your product-market fit and the effectiveness of your go-to-market strategy. Nail these elements, and you'll be well on your way to funding. 🚀 Hope this helps. _____________________________- Helping serious technical founders get out of sales and get funded.

Your business needs you to stop trying to do everything.  9/10 technical founders are stuck doing everything… a problem of their own making. We all slip into ‘get it all done’ mode from time to time. For those that this is your default,  it’s why you are stuck. If you do not address this, well, get ready for a long road of going nowhere. Hard truth: Juggling too many priorities isn't a badge of honor; it's a recipe for burnout, missed opportunities, and why you and your business are stuck.. And it only gets worse.  Here’s the science: Cognitive overload: ↳  Your brain's a powerful machine, but it's not designed for constant multitasking. Too many tasks lead to decision fatigue and diminished performance. Stress and anxiety: ↳  That nagging feeling of "I'm not doing enough" triggers a stress response. Cortisol levels spike, anxiety sets in, and your mental health pays the price. Procrastination and paralysis: ↳  When everything feels urgent, nothing gets done. You end up procrastinating on the critical tasks that actually move the needle. Killed creativity: ↳  A cluttered mind can't innovate. Overwhelm stifles your ability to generate new ideas and solve problems effectively. 4 steps to break the cycle: 1\ Ruthless prioritization: ↳  Identify the 2-3 things that will truly drive your business forward and focus your energy there — you already know what they are! 2\ Time block: ↳  Schedule dedicated blocks of time for those critical tasks. Treat these appointments as sacred and protect them fiercely. 3\ Stop saying yes: ↳  It's not rude; it's strategic. Politely decline requests and opportunities that don't align with your top priorities. 4\ Done is better than perfect 💡💡 ↳  Strive for excellence, but don't let perfectionism paralyze you. Ship it, iterate, and improve. Your mental health is your greatest asset. Protect it, prioritize, and break through that $1M ARR ceiling. Hope this helps. __________________________ I help technical founders get out of the day-to-day and get funded