Introduction
Growing a sales team isn’t just about hiring more reps. If you don’t have the right strategy in place, more bodies won’t help. In this convo, I sat down with a fractional sales leader to unpack the real drivers of sales growth, and the 4Ps every founder needs to get right.
Let’s start with, tell me what it is you do.
I’m the co-founder of Libra Partners, a sales consultancy firm that works with small to mid-sized B2B companies, often in fintech or software, helping them with sales strategy, sales management, and international expansion, the latter being mostly foreign businesses looking to enter the U.S. market.
Most of my work however is domestic and focuses on companies that have had some success but are struggling to grow. Often, the CEO is still managing the sales team, which typically has 3–4 people.
That’s fantastic, I especially like that niche around U.S. expansion—it’s not something many people offer. So, let’s say I open my CRM and see a dozen people who do what you do. What’s the special sauce that Libra brings?
Depth of experience. I’ve built 18 sales teams and served on the boards of 8 companies, working across startups, growth-stage, and publicly traded firms on three continents. Because of that, I don’t just look at sales, I evaluate how sales fit into the broader business, and I often end up advising on operations, finance, or go-to-market strategy because I’ve seen how all the pieces connect.
That’s great, but where do you draw the line? I absolutely know how easy it is to get pulled into ops or sales conversations. How do you stay within scope?
My experience helps me recognize issues outside my core expertise, but I don’t try to solve everything myself. I bring in people from my network, like if a company needs financial leadership but isn’t ready for a full-time CFO, I’ll recommend someone like you. Or if there’s a need for sales training, I will bring in a specialist.
That’s interesting, you don’t handle sales training yourself? Is that by choice, or do clients just not ask for it?
It’s by choice. I recently worked with a company that had 4 underperforming sales reps. I evaluated the market and restructured the team, developed a sales process, implemented a CRM, updated comp plans, and realigned territories and key accounts etc. Essentially, I developed the sales strategy, but the junior reps needed skill development. I could’ve trained them, I’ve done that plenty, but I brought in someone better suited. I know a few exceptional trainers with proven methods, and I’d rather have them do it right.
Are those trainers independent? I assume they follow your lead on strategy?
Yes, I set the strategy and brief them, so the training aligns. One I work with often creates her own training approach that combines elements from Challenger, SPIN, and others. She trains and then stays on to coach, which is rare and really effective. I trust her to get results, and clients appreciate that kind of seamless collaboration.
Besides international expansion, which is more niche, what are the top three pain points that companies usually come to you with?
I’d call them “symptoms” more than pain points.
- A full sales pipeline that’s just… stuck. Nothing is moving, and the CEO or founder can’t figure out why. On the surface, it all looks fine. Lots of leads, a busy team, but nothing is closing.
- They want to grow their sales team but don’t know how. Should they split territories? How do they structure compensation? Do they promote someone internally or hire a manager? They know they need to scale but aren’t sure how to do it effectively.
- They’re launching a new product or moving into a new market, say, from financial services into healthcare, and they have no real sales strategy for that shift. They’re not sure how to target the right customers, structure the team, or even assess if their current sales org is built for the task.
All of these situations come down to one thing: the CEO or founder wants to grow, but they either don’t know how to do it or what’s blocking that growth.
So what does a typical engagement look like? Are you in for a short, focused sprint or more of a long-term advisor?
It depends on the client’s needs, but I always start with a detailed assessment of their revenue, organization, and motion. At the end of that diagnostic, I deliver a detailed report that outlines what’s working, what’s not and most importantly, a phased action plan for fixing it.
So your standard consultant answer is “it depends”, but the difference is, your process is consistent and grounded in experience.
Right. What I described just now is the typical flow. I don’t do light-touch, pre-prescribed fixes. A lot of founders think they know exactly what the issue is and just want someone to execute their fix, but that’s not how I work. If they’re not open to a proper diagnostic and strategy, I’d rather refer them to someone else.
I’ve always respected that you’re firm in what you do and what you don’t.
Exactly. If I can’t help, I’ll refer someone who can. In fact, I just did a webinar with a fantastic marketer, and we talked about one of the biggest pain points we see, which is a misalignment between sales and marketing. It’s shocking how common it is—two teams working toward the same goal, but completely out of sync.
And here’s something else. The fractional sales space has exploded, but not all experience is created equal. A lot of people out there are former mid-level managers at places like Google. They say things like “I grew revenue by X%” or “I managed a team of 20.” But they did that at one of the world’s most successful companies, often with massive infrastructure and safety nets.
That’s not the same as building a startup from scratch, being acquired multiple times, sitting on boards, surviving downturns, and still figuring out how to keep the business afloat. That’s the kind of hard-earned experience I bring—and that’s what clients are really buying when they work with me.
It’s so interesting that you say that because a lot of people make the leap from big corporations into small business, and they don’t realize how different it is. I’ve done finance my whole career, but when I started working with smaller companies, I had to rethink everything. It’s not just the little things you take for granted, it’s the fact that everyone’s wearing five hats, and you’ve got to make tough decisions with limited resources. You really can’t understand what that feels like until you’ve lived it.
Totally agree. Let me give you a perfect example. I’m talking to a company right now, doing about $30 million in revenue, so a good-sized small business. They’re hiring their first senior salesperson after building the whole thing through referrals.
They told me, “We want someone who can sell to enterprise clients, build channel partnerships from scratch, and eventually lead and build out a sales team.”
I had to stop them. I said, “Hold on. You’ve just described three different roles.” A top-performing enterprise seller, a partnership builder, and a future head of sales. Those are different skill sets.
And the risk is that they make it worse by hiring someone from a huge corporation, thinking, “They’ve got a killer network, they know how to sell.” But those folks are used to big support teams and lots of infrastructure. Drop them into a small business where they have to do everything themselves, and it often falls apart, not because they’re bad, but because they’re just not used to it.
We see the same thing in finance. A founder’s ready to hire their first person, and they say, “I want someone to do X, Y, Z, and also A, B, and C.” But if someone’s really good at X, Y, and Z, they probably aren’t great at A, B, and C. It’s about prioritizing what’s most important.
Exactly. The guy I was advising said, “You’re right. I just described three different jobs.”And I said, “So now you’ve got to pick what’s most important.”
Yes! It’s such a shame when someone’s brilliant at what they do and then we promote them to manager, assuming they can teach others to do the same. But managing and mentoring require completely different skills.
Absolutely. Not to toot my own horn, but I lived that. I was the top salesperson in my company, then got asked to lead the UK sales team. I happened to do very well because I’m empathetic and intuitively know how to motivate people, but a lot of top salespeople aren’t wired that way, they thrive on the hunt, on closing deals. They’re individual contributors, and they love that. But what happens when you make that person a manager? They struggle. They compete with their team instead of leading them. They lack the systems thinking and the tools to scale what they do. It’s not that they’re bad people, it’s just that management is not their thing.
Let’s say a founder comes to you and says, “I’ve got this amazing salesperson. Frank is killing it. He gets our product, crushes his pipeline, and closes deals. Should we make him a manager? Or how do we make another Frank?” Do you help with that?
Absolutely! First, they need to be clear on what they are trying to achieve, as well as be aware of the opportunity costs associated with any decision. If they’re looking to replicate success, build a team around Frank, in the first instance, they need a proven, repeatable sales process.
And I don’t mean a script, I mean an actual process that works. That’s your foundation. With that in place, you can hire more people, plug them in, and know they’ll succeed. You tweak and refine as you go.
Now, if the question is whether to make Frank a manager, don’t rush into that. Even if you’re building a team of four or five salespeople, you probably don’t need a full-time sales manager yet. This is where fractional leadership is a smart play, you get seasoned experience at a fraction of the cost, without the risk of promoting someone who might not be ready or interested.
I help clients figure all of this out: compensation models, commission structures, defining territories, deciding who focuses on new business vs. account growth, whether to organize by product lines, it all depends on where they are and where they’re trying to go. And yes, this is the stuff I’ve done again and again.
It’s been such an interesting economic environment over the past six months, it’s kind of upended the typical sales flow. Honestly, the typical anything. I don’t know anyone who hasn’t been touched by this, whether directly or through downstream effects on their clients. So, what do you advise businesses that have had a tried-and-true sales methodology for years, and suddenly… it just stops working?
Yeah, that’s a tough one. I wish there were a silver bullet, something simple like, “Just do this, and it’ll all be fine”, but it doesn’t work that way.
It really depends on where your business is in its lifecycle and how it’s structured. If you’ve got existing clients, and you’re in this uncertain landscape (and I agree, it’s very uncertain right now), the best thing you can do is focus on retention.
Clients are pausing decision-making across the board. There’s talk of a recession. Some businesses are worried about tariffs. Even if you’re not directly impacted, that fear can affect everyone.
So, first and foremost, make sure your existing clients are happy. In SaaS, that’s called churn prevention. If they already like you, maybe there are additional services or products you can offer them.
Now, if you’re thinking about growth, especially in this climate, you need to ask: What’s the real value of my product or service right now? And can I position that value in a way that feels relevant?
I was recently chatting with the CEO of an outsourced sales agency and I told him, “Now is your moment.” Hiring a full-time sales rep in fintech, for example, could cost a quarter million dollars by the time you’re done onboarding. But outsourcing? That’s lower risk.
So yes, it’s about understanding your ideal customer, identifying their needs in this exact moment, and then communicating how your offering solves a problem—especially because of the current climate.
Totally agree. There’s no one-size-fits-all answer. We’ve seen clients approach this in so many different ways, so it’s hard to know what to tell them. It’s hard to instill confidence right now.
And honestly, one of the worst decisions a company can make, though I get why they do it, is mass layoffs. Marketing is usually the first to go, and that’s often a mistake. If your marketing team is good, they’ve got momentum, and when things turn around, it’s really hard to get that momentum back.
If you can avoid letting people go, you protect your institutional knowledge, your processes, your brand awareness, all of it. Instead, ask: Where is our revenue really coming from, and how do we grow that in the most cost-effective way?
Sometimes, that might not even mean acquiring new clients. It’s more about being strategic with what and who you already have.
I’ve often clashed with sales leaders when I was in-house because I’m naturally realistic (pessimistic =) and salespeople are optimists and sandbaggers by nature.
But that’s why I’m always pushing clients to keep operating expenses low from the start, so they can weather this kind of environment.
I always feel bad because I can’t drive the top line like you can. I can’t bring in revenue, so it’s hard to give guidance when things slow down.
Totally. But your role is just as critical. You’re the one protecting the business, making sure there is a tomorrow. That’s exactly the kind of balance I’ve seen play out again and again on boards. The CFO says, “We’re spending a lot on sales and marketing. We need results.”
So I, as a sales leader, have to look in the mirror and ask: Are we focused on the right things? Are the right people in the right roles? Can we pivot or reassign before we even think about letting someone go?
Because yes, sometimes you do have to let people go. That’s reality. But before I do that, I always ask, have I evaluated every avenue available to me.
One thing I see often when companies are hesitant to let people go is that they start combining roles or giving people responsibilities outside their zone of excellence to justify keeping them on. I get it, I’m not judging. But the reality is, that person usually struggles with the new tasks, has less time for their “regular role” and they start to suffer there as well.
Totally. I’ve seen something similar during aggressive growth phases. Leadership often says, “Let’s grow revenue, go hire more salespeople.” And I say, no. First, let’s look at who we already have. Are they fully utilized? Do we have a solid sales process? Are the right leads coming in and being closed? If not, hiring more people will just waste money. Then we’re in trouble, and Jennifer’s calling me a year later saying, “We spent all this money and nothing changed!” Whether you’re shrinking or scaling, the same principle applies: be thoughtful and efficient with the resources you already have.
Exactly. When things slow down, it’s a great time to do some housekeeping. Document processes, evaluate what is working. You can’t control the external environment, but you can control how you respond to it. When clients call me freaking out, I say, “There’s not much you can do about global fluctuations, but you can tighten up your internal operations.” I love your idea of looking at each person and asking, “Are they in the right seat?” How do we optimize the team we already have?
Yes, and can we invest in them? Coach or mentor them? If you put someone into a management role, help them succeed in it. Don’t assume they’ll magically know what to do. And yes, sometimes, after trying, you realize it’s not a fit and need to let someone go. It’s hard, but necessary. Whether you’re expanding or contracting, efficiency and effectiveness of your team are key.
Is there anything I didn’t ask that you’d want people to know?
Simon:
Yes. I use a framework I have developed over decades called the Four Ps of Revenue Growth:
- People: Are the right people in the right seats, and are they compensated well?
- Product: Does it have market fit? Are we targeting the right audience?
- Process: Are there strong sales and revenue-generating processes in place?
- Price: Is the pricing strategy aligned with how your customers want to buy, whether that’s SaaS, monthly billing, etc.?
Any one of those pillars being off can hold you back. I use the Four Ps to analyze sales organizations, and it’s been effective for decades. It may sound self-promotional, but it really works.
Hey, this should be self-serving it’s about you!
Fair enough! But really, it’s about helping companies make smart internal changes. I’ve seen big gains come from relatively small, focused shifts. For example, I worked with a 20-year-old company doing $4–5M annually. They had four salespeople, but the CEO was still the top seller and frustrated about it.
I came in, did a win-loss analysis, evaluated product performance and market perception, implemented HubSpot, ran weekly sales meetings, revamped their comp plan, and most importantly held everyone accountable. Weekly check-ins like, “You said you’d do X, did it happen? If not, why?”
After a year of just five days a month with me, their revenue grew by 63%. No new hires, just optimization. That’s what I mean when I say: look inward. There’s often so much untapped potential within the existing team. And if you don’t know how to unlock it, bring in someone fractional—me or someone you trust—who does. It makes a huge difference!
That’s such a great example. I completely agree, small changes can drive major results. Not everything requires a huge investment. In lean times, it’s about being creative. But accountability? That’s always in style, bull market, bear market, any time, any discipline. I really appreciate you doing this.
Conclusion
Sales growth doesn’t have to be a guessing game. Get your People, Product, Process, and Pricing in sync, and you’ll build a team that scales. Want help mapping this out for your team? Email Simon at simons@librapartnerssolutions.com, check out his LinkedIn profile or watch the Salty Sales Sages on YouTube.
