Stearns’ Post

In the fast-moving environment of investing in privately owned companies, flexibility is often the difference between success and stagnation. For private equity and venture capital firms, understanding how to harness flexible leadership when scaling operations or addressing underperformance is crucial for driving sustained growth. Here’s how to think through optimising leadership flexibility: 🚀 Scalability at Your Pace For growing businesses, marketing needs can change rapidly. Whether it’s a product launch, a pivot in market strategy, or responding to new competition, scaling your leadership resources should be dynamic. Consider bringing in executive-level marketing expertise on a flexible basis, which allows you to adapt to changing business priorities without the long-term commitment of a full-time hire. 🔧 Troubleshooting Underperforming Campaigns When marketing campaigns aren’t delivering expected results, speed is critical. Instead of spending months on a hiring process, consider tapping into leadership that can quickly diagnose issues and implement new strategies. This quick adaptability ensures that marketing campaigns are aligned with business goals and market realities, minimizing lost time and revenue. 📊 Data-Driven, Agile Decision-Making Flexibility also means being able to respond in real-time, based on performance metrics. The key to success lies in having the right leadership to continuously monitor data, adjust strategies on the fly, and keep your marketing initiatives on track. This approach keeps the focus on growth while remaining agile enough to adapt to new opportunities or challenges. 📈 High-Impact Growth with Long-Term Vision The right leadership approach isn’t just about solving immediate problems. It’s about balancing tactical execution with a long-term vision for growth. The flexibility to switch between short-term initiatives and long-term strategic goals allows companies to address current needs while setting up for sustainable growth. Practical Example: Imagine a portfolio company launching a new product that initially underperforms. By quickly adapting the marketing strategy, perhaps by testing new channels or refining the messaging for a different audience, the business can get back on track, optimising resources and minimising impact on overall growth. Is your portfolio company facing similar challenges with scaling or marketing underperformance? If so, consider how flexible leadership could play a role in pivoting quickly, optimizing efforts, and driving long-term success. Let’s discuss how you can apply this approach.

Are you one of them? (Read to the end to find out) Things I wish I had known early on in my first VP roles and my first startups: New Hire Tenure: Account Executives at pre-seed or seed-stage companies typically stay 12-18 months. Turnover Cost: Replacing these roles can cost 1.5-2 times the annual salary, or $105,000-$140,000 for a $70,000 position. Quota Attainment: New hires in early-stage companies often reach only 60-70% of their sales targets due to evolving strategies and limited resources. Early Stage Success starts with a Strong GTM Strategy Raising the Next Round: Companies with strong GTM strategies are 30-50% more likely to secure Series A or B funding. Stage-Specific Needs: Early stages need tactical execution and experimentation, not just scaling. Flexibility: Early stages need agility, which fractional leaders provide. Foundational Development: Building a solid foundation with fractional leaders prepares the company for future scaling. Investors prefer early-stage companies with robust GTM strategies. Instead of a full-time Head of Sales, focus on building a solid GTM foundation with fractional leaders to drive initial growth and future success. This will help your team succeed and set up your future leaders for success. Are you an early-stage startup building your first Revenue or GTM team? Rocinante can help you succeed from day one. We provide fractional leadership to ensure your first hires excel, crafting GTM strategies and scalable revenue frameworks. Let’s build a strong foundation for growth and market success. Ready to get started? Connect with me to see how Rocinante can boost your revenue journey. Over the next two months, I'm taking on a few new clients! #GrowthStrategy #RevenueAcceleration #StartupSuccess #GTMExpertise #FractionalLeadership #StartupConsulting #ScaleUpStrategy

Each growth stage requires different skills and experience - but there's a good reason you should have a single leader driving GTM across your entire company As your company grows, the expertise you need changes dramatically. 📈 When you're scaling from $1M to $10M, you need people who can drive 200-500% YoY growth—the ones who know how to take risks, build processes from scratch, and iterate quickly. But when you hit $100M or more, the focus shifts to 10-20% YoY growth. Now you’re hiring people from large companies who have a different mindset: 💠 Optimise what exists 💠 Repeat the playbooks that got them here 💠 Avoid taking bold risks. ⚠️ Here’s the problem: If you bring these “big company” leaders in too early, they’ll default to safe, incremental improvements. That’s not what you need when you’re trying to hit aggressive growth goals. Brian Chesky at Airbnb learned this the hard way. He brought in seasoned execs to run his teams, and quickly realised something was off. Over-delegation led to detachment from the core areas that mattered most. The result? People further from the leadership team relied on conventional, low-risk playbooks instead of innovating. In B2B SaaS, the same thing happens in GTM. Mid-level managers, far removed from leadership, play it safe—using strategies designed to avoid scrutiny, not to accelerate growth. And guess what? Your GTM efficiency tanks. 🔑 Here’s the takeaway: If you want explosive growth, you need to stay engaged in your GTM strategy. Don’t delegate too soon. Get in the trenches, challenge the conventional wisdom, and push for strategies that will actually move the needle. Ensure you have a single vision driving your whole of company Go To Market. Scaling isn’t just about hiring the right people. It’s about knowing when to hire, and when to stay hands-on.

The worst advice CEOs get? "Hire great people and get out of their way." Sure, it sounds great on paper. You're the humble leader giving complete autonomy. Your talented team has the freedom to be creative. Everyone's happy. Except it's a fairy tale. I know because I've made that mistake before. Here's what I've learned as CEO of Privy: Autonomy without alignment is worthless. If you're in a kayak with another person and both of you row as hard as you can with perfect form...but in opposite directions? You're not going anywhere. So I use what I call the Decision Tree Framework with every leader I hire. I heard about this from the former CTO of Shopify. It's simple but powerful. Picture a tree: ➝ The roots are decisions we always make together. They're irreversible and can cause major harm to the company if we get them wrong. ➝ The trunk represents decisions where leaders need to share their assumptions and get feedback before acting. These choices have broad company impact. ➝ The branches are decisions to make and tell me about after. I want to hear your thinking. ➝ The leaves are fully autonomous decisions. They're reversible, so act freely. This framework is about clarity. Every decision gets the right level of input, at the right time. Here's why this matters: If you tell your team to "improve revenue from existing customers," watch how differently sales and customer success interpret it. ➝ Sales pushes new product lines ➝ Customer success focuses on reducing churn Both help revenue, but now your teams are fighting each other. Once you set the decision tree framework in place, the next best thing to do is encourage your team leads to get intimately involved in the details. Not to micromanage—but because true alignment requires getting into the weeds. The goal isn't to solve my problems or have my team take things off my plate. It's about leverage. And leverage only works when everyone's pulling in exactly the same direction.

Last week I saw a post from a notable CEO that said, “90% of early-stage startups' growth problems can be solved with the right tech + process in place”. This is the WORST ADVICE I’ve seen on Linkedin. Here's why: All GTM problems are either people problems or problems you don’t yet realize are people problems. While we sell software, all of us leaders are really in the PEOPLE MANAGEMENT business. Software and processes don’t have feelings. Folks who focus all their time and energy on tech/tooling do that because managing people is HARD. Spending time on tech and process is not. The issue is that most leaders have never been formally trained in managing people and at rapidly growing companies, don’t have tons of experience nor practice. Which leads to two core issues: (1) They are both afraid to give real feedback and therefore don’t hold people to high enough standards (2) They lack the framework to approach coaching and skill development For new leaders, or those trying to improve people management skills, comment “people” below (or DM me) and I will send you two frameworks to approach this issue. One is very popular within the lineage of the best sales leaders in tech and the second from one of the top SDR leaders in the game who has built and managed teams of 100s of reps.

In my years working in B2B SaaS I’ve seen the same story play out again and again: Talented leaders—CMOs, CROs, and VPs of Sales—get fired for “failing to deliver.” But the truth is, they were set up to fail from the start. The problem isn’t the people. It’s how companies plan, measure, and run their go-to-market strategies. These systems are often broken at their core. Board members show up once a quarter, drop irrelevant advice, and vanish. CEOs get swayed by their networks, chasing trends or easy answers instead of digging into the hard realities of their business. GTM strategies get built in spreadsheets and fantasy models, disconnected from the actual market, customers, and teams. This doesn’t work. It never has. 😤 When the framework is broken, no amount of talent can save it. Leaders get blamed, teams lose trust, and companies waste time and resources chasing fixes that don’t address the root issue. ✅ Here’s what needs to happen: First, boards & investors need to step up. Their job isn’t to sit on the sidelines. They need to engage, open doors, and provide real help that moves the business forward. If not, GTFO of the way and we'll see you come exit time. Stop overvaluing your money. Second, CEOs need to take responsibility. Stop leaning on biased networks and buzzwords. Start building strategies based on real insights from your market and your teams. There's no more room for the classic excuses of "not knowing what XYZ department does, but I respect what you do". 💩 💩 💩 Lastly, GTM strategies need to reflect how business actually works. That means using real data, creating shared accountability across the entire team, and treating the plan as a living, breathing process that evolves with the market. This is how you win. This is how you avoid burning out great leaders and leaving value on the table. You can’t build a business in a spreadsheet. It’s time to hold the process accountable, not just the people. I'm proud to say I've lucked out this time with my current company that has a CEO who arguably knows every aspect of the business better than anyone else. He keeps me sharp and on my toes in the best way. He's a team mate as much as a team lead. ✌

Interesting post- also applies to building medical practices.

In the past 18 months, I have built, launched, and led a bootstrapped company (Nova Chief of Staff) that recently hit 1M in revenue. We're small but mighty, & we're just getting started. Many of you are here for the LinkedIn content, and I love that. But what am I here for? What are we planning in 2025? And... how can you help? 😇😇 A little bit of context... 14 months ago, a few smart people told me that if I was going to be selling a course & building a company, I needed to build a public personal brand at the same time. Since then, I have posted nearly every day about: - the Chief of Staff role - C-suite adjacent roles - two decades of people-leadership - becoming a new mom & entrepreneur - building Nova Chief of Staff, in public I speak to: - current & aspiring Chiefs of Staff - Senior EAs looking for a path to level up - folks learning to differentiate these important roles - & business leaders learning about the power of a Chief of Staff And I have grown by about 25k followers in the last year. As we approach 2025, Nova Chief of Staff - like many companies - is deep into next year's planning. Here is what you can expect from us: #1 Acclaimed Chief of Staff Certification Course 🌟 -Our flagship product with 800 students across 23 countries & rave reviews—it’s not slowing down anytime soon. - In 2025, we’ll have AI feedback for assignments, a new Slack channel, and other exciting enhancements! -Enrollment increases by $400 in January—secure your spot now! https://lnkd.in/ekBc2Q5R #2 B2B Efforts ☎️ - With our course's major success, it’s time to shift focus to B2B. - What’s wild? We’ve got 5, 10, even 20 people from the same companies who enrolled separately—mostly via word-of-mouth (so cool!). - Now, we need to help companies enroll their teams. B2B is a relationship game, and I lack direct ties to CHROs and CEOs at major companies. - Suggestions? Contacts? B2B experience? I'm ALL ears! #3 Recruiting 👥 - With thousands of Chiefs of Staff and strong leadership ties, it’s time to grow the recruiting side of our business —plus, I love it! - I’ve hired & led hundreds in my career and know exactly who’ll succeed as Chief of Staff, matching leaders with the right fit. - Keeping this tight: 1 search per quarter, DM to join the waitlist. #4 In-Person Course 🎓 - Finally, we have THREE more in-person courses planned for 2025! With RAVE reviews from our October conference, we can't wait for more. - Learn more: https://lnkd.in/gHPzUJkv (already 20% sold out!) #5 TBD: Chief of Staff Industry Tracks 🤓 - Startup, government, sports, edu, healthcare? Working with some great partners to line up industry cohorts to supplement our course in 2025... tbd! 💙 _ As a first-time entrepreneur running a first-of-its-kind company - I am HERE for all the support I can get. And, building in public just feels right. Thank you for being here! Team Nova

2024 has been a WILD ride for my career and personal development. When job searching I narrowed down my search to my next dream role and instead of looking for titles, I looked for culture and values: ✅Woman-owned business ✅People and relationships based ✅Leadership ✅Continued professional and personal development opportunities ✅Transparent communication ✅Innovation and creativity Would be cool if it incorporated things I enjoy: 🎤events 🏐sports 🧾sales & marketing 🌟hospitality Where I can flex my superpowers of empathy, adaptability, and collaboration. Where I can play the role of Glinda the Good Witch and support and mentor folks who don’t realize that they have what it takes to level up in their career. Or give them some warning signs of pitfalls I’ve experienced. Would be cool if I could touch and build a lot of things and pass them off to specialists to give it life. Enter Nova Chief of Staff. This time last year I didn’t even know it existed or what a Chief of Staff outside of West Wing actually did. But none of that mattered because when I met Maggie Olson, things just clicked into place and ALL the things I had been looking for, manifested into a role I am incredibly grateful to have. (Thank you, Maggie!) My hands have been up in a victory pose ever since. Check out what we’re planning for 2025 in Maggie’s post! If you think your teams could benefit from some excellent executive support training or you are just curious to learn more, follow us and reach out to connect. Be kind to yourself and others. ❤️ You are worth investing in!

"Hiring a fractional leader means that you can offload meaty initiatives to an experienced resource who requires minimal onboarding." Just one of the many reasons that companies leverage a fractional resource. Solid article outlining why (and when) companies lean into this model. #executiveleadership #startupsupport https://lnkd.in/gdBHBqrX