Founder-led-to-repeatable sales ⚙️
Founder-led-to-repeatable sales ⚙️
A year of selling process-fully, how an AppSumo launch led to a bootstrapped “seed fund”, and a reminder on being more determinedly vocal about your startup’s premise.
Welcome to the 86th edition of The SaaS Baton.
A fortnightly newsletter that brings you hand-curated pieces of advice drawn from the thoughtful founder-to-founder exchanges and interviews taking place on Relay (curated with 💛 at Chargebee for Startups) and the interwebz. So, stay tuned! And thanks for reading!
In this edition, you’ll find the following instructive and inspiring pickings:
#1: Warmly,’s co-founder and CEO, Maximus Greenwald, briefly catalogues the strategies, experiments, questions, tools, and people that drove each of the four quarters of establishing an early-stage (spanning: 0-100+ paying customers) sales motion.
#2: Paperform’s co-founder, Dean McPherson, describes their foundational AppSumo launch and addresses the assumed skepticism that often surrounds that platform and its value-conscious users.
#3: Vanta’s co-founder and CEO, Christina Cacioppo, notes how an (all too) hushed focus on building out an inventive, first-mover offering produced astonishing outcomes (ex: $10m in ARR prior to a series A raise) but also came at a serious cost (“…gave the impression [that] we were smaller or less ambitious than we really were”).
Finding these discerning founder takes valuable? Please consider sharing this edition with an ever-curious teammate or a much-cherished SaaS friend. 🙂 New readers can sign up here.
#1: Founder-led-to-repeatable sales ⚙️
(From: Warmly,’s Maximus Greenwald) (Source: LinkedIn)
Warmly, went from 0 to 100+ paying customers in 2023. More importantly (for the hyper-critical founder inside me) we went from founder-led sales to a repeatable sales process.
Here how I (tried) to build a repeatable sales motion this year:
Overview:
↳Q1: Founder Led Sales
↳Q2: Sales-Leader Led Sales, Founder Involved
↳Q3: Seller-Led Sales, Founder Involved
↳Q4: Seller-Led, Sales Leader Run
Q1: Founder Led Sales
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↳👨👩👧👦 Customers: 0-10
↳⚡️GTM Strategy: Design partners & founder friends
↳📈 Key experiment: messaging
↳❓Key questions: (1) can we sell this thing at any price point? (2) can I stand up a basic funnel? (3) can I find 10 most common objections and solve them?
↳🛠️ Key new tools: HubSpot (CRM), Mixmax (SEP), ConnectTheDots (Warm Intros), DocuSign, Spreadsheets
Q2: Sales Leader Led, Founder Involved
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↳👨👩👧👦 Customers: 10-30
↳⚡️GTM Strategy: Founder friends & startups, email sequencing
↳📈 Key experiment: LinkedIn sequencing
↳❓Key questions: (1) can a strategic sales leader who is a non-founder roughly hit projected quota? (2) can I as the founder hit quota and also reasonable terms (no opt-outs, annuals only, discounts)? (3) can I build trust with this leader to sell my vision and build a team around them?
↳🛠️ Key new tools: Warmly/6sense (Website de-anonymization), Warmly (AI Website Chatbot), Outreach (SEP), Seamless.AI (ContactDB), Sendspark (video-personalization), Warmly/Salesflow.io (Auto-LinkedIn sequences)
↳🤠 Who: Max, Keegan, Nabil
Q3: Seller-Led Sales, Founder Involved
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↳👨👩👧👦 Customers: 30-60
↳⚡️GTM Strategy: Omni-channel (linkedin/email), inbound (Warm Calling on the website with Warmly), territories
↳📈 Key experiment: Conferences
↳❓Key questions: (1) can an AE and ISR ramp and hit quota in the last month of the quarter? (2) can our sales leader enable the sellers to ramp and hit quota? (3) can we build a V1 sales process that can be understood and executed?
↳🛠️ Key new tools: Warmly (AI auto-emails), Warmly (AI auto-linkedin), Hubspot Quotes, Tourial (Pre-made Demos), Spekit 🐙 (Sales Process documentation), AccountAim (Territory building)
↳🤠 Who: Katherine, Terence, Keegan, Nabil, Max
Q4: Seller Led, Sales Leader Run
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↳👨👩👧👦 Customers: 60-100+
↳⚡️GTM Strategy: No change from Q3 (repeatability!), just optimization
↳📈 Key experiment: Linkedin social to drive inbound
↳❓Key questions: (1) can I as the founder step away from closing altogether? (2) can the sellers hit quota each month across the quarter? (3) can we find repeatability in our core metrics (meetings held, SQOs, closed/won) and rates
↳🛠️ Key new tools: Letterdrop (LinkedIn Social), Alysio (Gamified daily sales metrics), Warmly, (Full cross-tool autonomous sales orchestration)
↳🤠 Who: Katherine, Terence, Keegan, Nabil, Max, Marijana
📝 Related Relay reading:
Wingman’s co-founder, Shruti Kapoor, on a (trust) prerequisite one must get right before implementing any sort of sales processes (“What people want to know is ‘will you be around in 1 year’ and ‘will this product actually work.’”)
Airplane’s co-founder, Ravi Parikh, on not overcomplicating the sales process with unnecessary specialization (“…the cost of specialization is that it’s a management overhead for you. And it’s also like communication overhead internally. You don’t want to pay those overhead costs until you absolutely have to.”)
#2: AppSumo buyers are “phenomenal early users” 🎯
(From: Paperform’s Dean McPherson) (Source: Relay)
We formally launched Paperform in December 2016 by running a life-time deal on AppSumo.
Running AppSumo deals is something I’ve been asked about frequently by other founders ever since — is it a good idea? How much money do you make? Does it help or hurt your business in the long run?
For us, in that time and place, running an AppSumo deal was an incredibly valuable exercise.
In the two weeks our deal was live (deals were much shorter lived, and ran one-at-a-time back then), we sold close to 3000 life-time deals, launched on Product Hunt, and became a real business.
By March, three months later, we quit our jobs — the cash from the deal was our “seed funding”, it helped us bridge the gap between our MRR coming in the door and our projections of when we’d be Ramen profitable.
Even more beneficial than the cash in the long run though were the users.
Of those 3000 users who made the purchase, at least 1000 redeemed their accounts on day one, jumped in, and started using Paperform for work. For early-stage software, there is nothing more valuable than having actual people trying the product for real-world use cases.
The average AppSumo buyer persona cops a lot of flak in the SaaS community.
On average, they tend to be: value conscious (AKA cheap), want everything for nothing, and are extremely demanding. These tendencies also make them phenomenal early users — if a feature is missing or broken, you hear about it.
These early adopters helped us carve out our product roadmap for the first year (at least) — because there was a critical mass of them, it made prioritization easy. If one person requests a feature, then it might be an OK idea.
If 30 people request the same feature, it’s obviously important.
Over the first year, we focussed on fleshing out the core functionality of the product based on the ongoing conversation we were having with our users, and in turn we continued to give these AppSumo users a better, more powerful product to use.
What a lot of SaaS builders miss about the AppSumo community, is that they’re often mistreated as consumers. They regularly get shafted onto plans that don’t receive updates, products that are shut down, or the deals simply aren’t honored.
By giving more and more value to the community we created a lot of good faith, and vocal supporters. To this day, some of our biggest product champions are people who have been around since the AppSumo launch.
On the other hand, companies who sell lifetime deals on a regular basis can’t help but look cheap themselves. From a brand positioning perspective, that could be a good or a bad thing. Some great companies position themselves around being cheap.
For us though, as we established ourselves as a competitive player in the form building space, and as a Product-Led company that values quality, we have stayed away from running deals since.
My only other advice for people around running lifetime deals is to consider what the ongoing costs look like for you to support that user base, be it headcount, technical debt, product complexity, or infrastructure costs.
Launching (and re-launching) on platforms was something we did a lot in the early days. We didn’t have any owned distribution channels, or large personal social followings, so that meant that we had to go and try and leverage other people’s audiences to spread the word.
In particular we ran a heap of Product Hunt launches 2 for all kinds of things: redesigns, e-books, new features. These stopped moving the needle over time — they’d still drive a little blip, but not enough to justify putting in a large amount of effort.
For new products without established distribution channels it’s worth the shot.
#3: “In a sense, we were too quiet” 📣
(From: Vanta’s Christina Cacioppo) (Source: The Generalist)
Prioritizing external communication is absolutely something that I think all founders and company builders need to be thinking about from Day 1 – even if you think you don’t need to yet.
From the early days of our security and compliance journey at Vanta, it was pretty clear that we had uncovered something a lot of people wanted. Because of that, we were intentionally under the radar as we built, tuned, and refined with customers – all with the goal of finding product/market fit before even really going to market.
In my career, I’ve found the easier part is building a product. The hard part is building something people want. So, we focused first and foremost on validating ideas and narrowing in on something people wanted.
We started with SOC 2 automation, and we quickly realized it was a deep and valuable problem applicable to every company – but everyone else thought SOC 2 was this tiny, niche back office process about which only big companies cared.
We purposefully stayed quiet as we built product and distribution so we could get as far ahead as possible because we knew once the secret was out, copycats would come.
And in many ways it worked – we got to $10 million in ARR before taking a Series A and had over 600 customers before we even had a real website.
On the other hand, for those outside of Vanta, our under the radar approach gave the impression we were smaller or less ambitious than we really were. In a sense, we were too quiet: I thought that if we put our heads down and did good work, positive word of mouth would follow.
And it did, somewhat, but I also let a vacuum develop that the copycats eagerly filled with their own half-truths and misstatements. The reality is that we always were, and continue to be, much larger than any of the inevitable copycats. But that didn’t always line up with how much, or little, people were hearing about us.
When I look back, customers and the market should have heard from us more. I didn’t appreciate how important external communication can be, especially with media, investors, and analysts.
At the time, if I was meeting with an investor for a speculative round years in the future, I wasn’t helping close a candidate we were excited about today, and that seemed like the wrong tradeoff.
Surely, I thought, the market would see our product improvements and understand our leadership position without my tweetstorms?
Some customers did, but many were busy building their own businesses. Looking back, I found it too easy to assume that outsiders would understand our vision and results because we understood them internally.
The last couple of years have taught me that communicating directly is often ‘important and not urgent,’ and it really matters.
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Thanks for reading! 🌻
Team Relay (Chargebee for Startups)