From Series A to Exit: Mastering Metrics
4/8: Sales - Advanced
10 Min Read – What You’ll Take Away
Scaling Sales is a transition, not a switch - build your playbook around ICP, messaging, and pricing before you start hiring.
Hiring at the right time matters just as much as hiring the right people - a key role today might be irrelevant in three years.
Align your Sales development focus with your funding stage - Series A is finding fit, Series B is optimizing motion, and Series C+ is capturing new frontiers.
RevOps isn’t just reporting - it’s the engine that refines your playbook.
Win/ Loss analysis isn’t optional - no idea why you win or lose and you’ll keep making the same mistakes.
Retention alone doesn’t cut it - grow existing business (NRR) with a clear land & expand strategy across all your functions.
Partnerships won’t fix bad Sales - if you can’t sell your own product, don’t expect resellers to do it for you.
Personal incentives matter - what may be good for your partner’s business doesn’t have to apply to its individuals.
From Series A to Exit: Mastering Metrics
Despite what you may think, the recipe for reaching your next financial milestone doesn’t have to be a black box. In “From Series A to Exit: Mastering Metrics”, we break down what it takes to position your business as an attractive investment - be it for funding or a strategic exit. Each article focuses on a core function critical to your success:
GTM: Sales - Advanced,
Customer Retention,
Finance,
and People.
In addition to my own experience, my co-authors draw on their success stories from the likes of Uber, Booking, Dropbox, LinkedIn, Just Eat Takeaway, Lightspeed, Miro, EasyPark, Bynder, Squarespace, BlackRock, JP Morgan, Ares, and more.
Missed Part One?
Last week had us go through the entire Sales funnel in the search of common mistakes and how to fix them. I also shared the latest version of my Sales Playbook so you can up-level yourself and your team.
But at some point, reaching for other echelons of scale goes further than just the quality of (individual) execution. Scale is in the agency of others. It’s our job to provide fertile ground (i.e. an org) that enables others to add value through individual contribution, collaboration, and further delegation.
GTM: Mastering Sales Metrics - Advanced
Still on with Just Eat Takeaway’s Richard de Veer and Miro’s Igor Madzura, this week, we’ll fire up the afterburners:
how to scale past founder-led Sales,
using the power of RevOps,
and leveraging partnerships for GTM expansion.
B. Scaling Past Founder-Led Sales
Going from founder-led to a professional Sales org isn’t a flip of a switch - it’s a transition. Before you throw serious headcount at scaling, you need to nail the fundamentals: moving from sheer Product-Market Fit (PMF) to an early stage of Go-To-Market Fit (GTMF). That means testing who to sell to (ICP), how to position yourself (value prop, competitive analysis, …), and what Sales motions convert best (playbook). You have to figure out what works and what doesn’t (RFW, RFL, conversion rates throughout the funnel).
This transition happens in stages. Your first key hires help refine the playbook and ensure deals close without your direct involvement. Only once that foundation is set, it’s time to scale headcount.
According to recent data from Carta, this shift is happening later than ever: in 2019, the median time from inception to first hire was 214 days - by 2024, that stretched to 284 days. The trend holds for second and third hires as well. Why? Tighter funding, AI-driven efficiency, and increased overall volatility forcing founders to run ultra-lean teams and prove traction before doubling down on expansion
1. Who to Hire and When: Building a Sales Org Over Time
Scaling a company means evolving. Yet I often see both founders and employees struggle with shifting corporate cultures. The reality? A role that’s crucial today might be out of place in three years. Successfully scaling, therefore, isn’t just about hiring the right people - but hiring them at the right time. Burn capital on enterprise AEs before a proven GTM motion and you won’t 10x revenue - you’ll just 10x your cost and chaos.
While you may be further along by Series A or B, the below hiring plan offers a rough guide on who to hire when - and what you need to get out of them.
Series A: True PMF & First GTMF
Founders often drive early Sales - scaling requires a Rep who can iterate fast and qualify well before a repeatable process is in place. Their resilience to “no”s and ability to dig for pain points will be the basis for finding true PMF.
First hire should be a strong full-cycle AE who thrives in ambiguity, is exceptional at discovery, and can work directly alongside the founder to refine ICP and messaging.
Series B: Scaling GTM & Optimizing Unit Economics
With a proven GTM motion you need a leader to standardize, scale, and introduce new best practices. As expectations rise, this hire must shape strategy, collaborate on TAM expansion, and mentor Reps as they start asking about career growth and personal development.
This also marks the shift from outbound-heavy to a balanced inbound-outbound motion. Pre-Series B, a 70-30 outbound-inbound mix is common. But post-Series B, an inverted split (30-70) signals true GTMF - where Marketing fuels demand, and Sales converts efficiently.
If you haven’t already hired a Head of Sales or lead before, now is the time to structure and refine processes, coach AEs, and implement best practices for outreach, discovery, creating urgency, and BOFU closing.
SDRs to lift outreach from AEs, enabling them to focus on closing.
Customer Success or Account Management (early-stage) to increase retention (churn) and up-sell opportunities (LTV, ARPA). Not only will this set the basis for NRR growth but will further lift a load off of AEs so they can focus solely on closing new business (land & expand).
RevOps to optimize processes, track conversion rates, and keep iterating your GTM playbook. They’ll also slice and dice your market to set the basis for international expansion and run joint GTM campaigns with Marketing (e.g. at Formitable and Convious we targeted specific competitors with a tailored limited-time offer and messaging). Their experiments and insights will prove invaluable as you try to flip your inbound-outbound split and spin your GTM flywheel past the speed of light.
Series C: Global Expansion, TAM Growth & Partnerships
By Series C+, retention has become an absolute core growth driver. By now (or even late Series B), expansion can no longer rely solely on net-new deals. Instead, growing ARR exponentially and organically comes down to retaining and growing existing customer relationships (NRR). Splitting Sales into new vs existing business isn’t enough: we need a clear land & expand strategy across Product, Marketing, Sales, Customer Success, and Finance - from acquiring customers with a wedge to systematically driving adoption, increasing usage, and layering on expansion revenue through up-sells, cross-sells, and strategic pricing. More on this, however, in our Retention article.
If your Head of Sales (New Business) isn’t thinking Marketing and Retention, it’s time for a CRO - one with a clear vision for NRR growth, TAM expansion, and partnerships on global scale. With exits now hinging on GTM performance more than ever, this hire has to lead you to the promised land.
Hire more Customer Success managers to fully execute on land & expand strategies (retention & up-sell).
Once you've set (regional) splits - especially with a local presence - you need (Regional) Sales Managers. Not only will they build local teams and adapt their outreach - they’ll act as cultural anchors in satellite offices. When hiring, make sure to pick leaders who truly know their market, understand regional nuances, bring personal networks, and have new insights for the organization. The same applies if you decide to go for vertical splits instead.
Once your own Sales motion is flying, it’s time to expand with Partnerships & Channel Sales to leverage indirect Sales motions (more on that further down).
2. The Power of RevOps
Reps chase bad-fit prospects, deals keep stalling for “other” reasons, and GTM teams operate in silos. If your pipeline is full of custom deals, if Sales and Marketing are pointing at each other, and if you can’t pinpoint why conversion rates are slipping: it’s time for RevOps.
“When revenue stalls despite adding headcount, the problem isn’t effort - it’s focus. On where you can win, win more, and faster”
Richard de Veer
Think of them as sherpas behind the scenes: guiding GTM teams with the right insights, structure, and alignment. They don’t just report on numbers; they provide the data to keep refining your playbook.
Which sales motions lead to higher close rates?
Which deals stall and why?
How can Marketing, Sales, and CS efforts be even better aligned?
Here’s a glimpse into the top challenges RevOps help solve - chances are, you’re facing some of them already.
Attribution is broken - buyers rely on dark social and peer networks, making traditional reporting unreliable.
“Traditional reporting can’t tell you what actually influenced a deal, making it impossible to know what’s working, what’s wasted effort, and where to double down.”
– Richard de VeerFix it: Implement win/ loss debriefs, track self-reported attribution (“How did you hear about us?”), and monitor community mentions and analyst reports that influence deals outside your CRM.
Not all revenue is created equal - if CAC is too high and LTV too low, every bad-fit deal you close just digs the hole deeper.
“Back when growth-at-all-costs ruled, any customer profile would do. But now, not all revenue is created equal.” – Richard de VeerFix it: Use RevOps to align Sales and Marketing on high-intent, high-LTV segments. Shift from broad targeting to smart segmentation that prioritizes quality over volume.
Win/ Loss analysis is non-negotiable - if “Other” is your top reason for lost deals, you’re avoiding reality.
“Most teams celebrate wins. But why did you win those and why did you lose others?” – Richard de VeerFix it: Enforce structured win/loss reviews. Identify real RFWs and RFLs - then iterate your sales motion based on those insights.
Data without insight is noise - a bloated dashboard won’t tell you why deals stall or which campaigns drive conversions. RevOps translates raw numbers into clear actions Sales, Marketing, and CS can actually use.
Fix it: Stop tracking vanity metrics. Focus on conversion rates, sales velocity, and multi-stakeholder engagement to pinpoint friction in your funnel.
Incentives drive behavior, but so does fear: if Reps chase bad-fit customers, they’re not reckless - they’re desperate.
“Incentives should reward pipeline growth, churn reduction, new logos, and expansion sales - since those drive sustainable revenue.” – Richard de VeerFix it: Diagnose why Reps cut corners: too few leads, misaligned targets? Adjust inputs before tweaking comp plans.
Structure beats scale - hiring more reps won’t fix inefficiencies. If deals keep stalling, adding headcount just adds overhead. RevOps ensures you optimize the process before multiplying the problem.
Fix it: Improve qualification criteria, eliminate stalled pipeline clutter, and create a data-driven feedback loop before scaling the team.
3. Key Metrics to Master Throughout the Funnel
The more senior we become, the more we get paid for the quality of our decisions - less so for the executional work we do. But good decisions require experience and the right insights. If you’re only tracking lagging indicators like closed deals or new ARR, you won’t know if your changes are working until it’s too late.
In last week’s article, we covered 18 fixes to improve your Sales performance. With the below leading indicators you don’t need to wait six months to see results. Track what’s working and where to adjust further at every stage of the funnel.
Attention (Prospecting): are we getting in front of the right people?
Connect Rate (% of successful connect attempts)– Do we have the right contact details? If it’s low, you’re reaching dead ends. You're either targeting the wrong people, using bad data, or your outreach method isn’t working. Validate contact data regularly and use tools like ZoomInfo, Apollo, or LinkedIn Sales Navigator. Segment by title, company size, industry, and buying intent. Use multi-channel outreach and don't give up: it takes 5-8 touchpoints to get a response - cold-outreach connect rates average only 3-8%.
Response Rate (% of outbound messages that get a reply): If it’s low, messaging is off or targeting is wrong.
Meeting Booked Rate (% of outreach sequences that convert to a first call): If this isn’t improving, your hook isn’t landing.
Interest (Discovery & Qualification): are we talking to real buyers with real pain?
Opportunity Qualification Rate (% of created opportunities that remain qualified post-discovery call): If it's too low (<30%), you're creating too many weak opportunities, disqualifying too aggressively, or suffering from a lack of TOFU volume. If it's too high (>50%), discovery calls aren’t rigorous enough, or Reps are too hesitant to create opportunities in the first place.
Pricing Discussion Rate (% of discovery calls where pricing is covered):If reps avoid pricing, they’re wasting time on bad-fit leads.
{Top RFL} Discussion Rate (% of discovery calls where {your top RFL} is actively addressed): If it’s too low (<20%), Reps aren’t addressing the elephant in the room. Too high (>60%) but no impact on closing rates and your RFLs need a re-do.
Decision (Objections & Closing): are we removing roadblocks and moving toward commitment?
Multi-Stakeholder Engagement (% of deals with 2+ decision-makers engaged): If <80%, Reps are likely selling to the wrong person and did poor discovery.
Solution Validation Rate (% of opportunities where prospects validate the solution after proposal is sent): If low <50%, Reps may be rushing to proposal stage before the prospect is truly bought in.
Action (Closing & Scaling): are we winning efficiently and setting up for long-term success?
Proposal-to-Close Rate (% of proposals sent that turn into closed deals): If this is weak, either pricing, urgency, or trust is off. Also worth checking whether your proposals follow the best practices.
Win Rate (% of qualified deals that close): If your win rate throughout the funnel is <20%, something’s broken in your GTM motion. Drill down on other metrics to identify where the drop-off happens. Adopt my playbook to fix it.
Sales Cycle Length (Days from first call to closed-won): If deals drag, Reps either aren’t pushing urgency or following the Playbook.
Renewal Rate (% of closed deals that get renewed after their initial term) and LTV: If this is <90%, you’re either winning deals with non-ICPs or your Customer Success Team needs to step things up. Either way, you’re killing your NRR growth.
Bonus Insights:
Skipped Playbook Steps: Check how many steps Reps skip per deal and correlate with win rates. My experience: more steps skipped = lower close rates.
Rep Activity Breakdown: Are reps evenly balancing activities across the funnel? If they’re only working deals already in pipeline, their upcoming quarter will be a bust. Coach reps on time management. If they’re spending all their time closing, they’re neglecting future revenue.
Renewal & Upsell Rates: Did customers stick? If time to go-live (TTL), renewals, and up-sells are weak, Sales is likely closing bad-fit deals.
4. Partnerships 101
If I had a dollar for every time a founder suggested to “just sell through resellers” once their GTM motion ground to a halt… Partnerships can accelerate your growth - not create it.
Finding out whether you’re ready for a partner Sales motion starts with gaining clarity on what type of partnership you’re actually looking for.
1. Finding the Right Match
Not all partnerships are created equal.
Integration Partnerships: Enhance your product by embedding it within another tool or platform. While API-first was once a priority in the SaaS world, recent trends favor all-in-one solutions over fragmented integrations - making this type of partnership less critical for many at the moment.
Referral/ Reseller Partnerships: Scale customer acquisition beyond your own Sales team by having partners bring in leads or directly sell on your behalf. This works especially well in industries where partners already have deep trust and relationships with your target buyers (e.g. upstream or downstream complementary solutions) or if prospects have determined one moment to buy the entire stack (e.g. as part of a tender).
Implementation Partnerships: Ensure customers get a level of service you may not be able to provide at scale. Think system integrators, consultants, or agencies that offer onboarding, customization, or managed services.
2. Before Expanding Through Partners, Nail Your Own Sales Motion
One of the most common partnership mistakes is relying on externals to do what you couldn’t do yourself: figuring out GTMF. If you don’t have a repeatable, scalable direct Sales motion, how can you expect an external team to succeed selling your product?
Before formalizing any partnerships, ask yourself:
Do we consistently close deals within our ICP?
Do we have proven messaging and positioning that resonates?
Do we have clear pricing and packaging that partners can easily sell?
“If the answer to any of these is no, focus on fixing your direct Sales first - partners won’t magically figure it out for you.”
Igor Madzura
3. Formalize What’s Already Working
Rather than hunting for external partners from the get go, start by looking internally. Chances are, your first partners are already hiding in plain sight:
Your Sales team might be getting referrals from consultants or agencies.
Your Go-Live or Customer Success team might be collaborating with implementation partners on onboarding.
Some of your larger customers might already be using your product alongside another, complementary tool - suggesting a good fit for an integration partnership.
“Start by identifying and formalizing these relationships before building new ones from the ground up.”
Igor Madzura
4. Making Partnerships Work Past the Paper
Signing a partnership agreement is easy. The real challenge is in joint execution - getting both internal and external teams aligned and motivated.
External buy-in: Your partners’ Sales reps need to understand, believe in, and be incentivized to sell your product. Remember: what may be good for a company doesn’t automatically apply to individuals - if they don’t see the value or don’t make money from it, they won’t push it.
Internal buy-in: Your team needs to be fully on board.
Product: Willingness to prioritize integrations.
Marketing: Dedicated co-marketing resources.
Sales: Understanding how to co-sell and up-sell partner solutions.
“Without the buy-in on both sides, partnerships fizzle out.”
Igor Madzura
5. As Always: Land and Expand
Once you’ve proven that partnerships work - meaning they’re bringing in or are attributed to significant pipeline and revenue - it’s time to scale:
Build a dedicated partnerships team to recruit and manage new partners.
Invest in partner enablement - creating training, incentives, and playbooks for external teams.
Expand into formal partner programs with tiered incentives and Marketing support.
Hire strategic leaders who can solve the buy, build, or partner puzzle - and make sure they have a voice in key decisions. At Lightspeed, initial partnerships with e.g. Chronogolf and ReUp eventually evolved into full acquisitions.
When executed well, partnerships act as a growth flywheel: scaling Sales beyond your team, providing new revenue channels, enhancing your product, and even seeding your M&A strategy. But jump in too early or fumble on execution and they become a costly distraction instead.
Need Help?
Already applying these best practices? If you’re wondering where your team stands or need a fresh perspective: I offer performance scans that pinpoint the gap between your status quo and your next financial milestone.
With years of experience advising entrepreneurs and leading businesses through multiple successful exits, I bring a unique toolkit of frameworks, strategies, and best practices to position you for fundraising or a strategic exit.
Let’s connect and explore how to set you up for your next major milestone. Happy to help you navigate these waters.
Coming Up…
The following 4 articles go into other core business areas and their most relevant metrics. Fueled with the insights of experts in their fields, they will help you get each business unit in shape for your next financial milestone. Next up is …
Learn how to build a product infrastructure that not only supports your own growth but addresses concerns of potential buyers - like IP protection, ease of integration, and technical scalability. We’ll touch on the balance between visionary innovation and customer-driven iteration to strengthen Product-Market Fit, expand your TAM, and create stickiness that drives long-term growth.