ProfitWell
profitwell.com · Founded 2012
ProfitWell is a revenue automation platform designed for subscription and SaaS (Software as a Service) businesses. Acquired by the Merchant of Record platform Paddle, it provides tools to track financial metrics, reduce customer churn, manage pricing strategies, and automate revenue recognition.
Built Enterprise Sales Motion That Increased Average Deal Size from $6K to $30K
When I was recruited to ProfitWell's Retain product team, the company faced a critical growth barrier: there was no dedicated enterprise sales approach in place. The product was being sold transactionally to SMBs, and we were stuck closing deals under $6,000 annually. Larger enterprise customers had fundamentally different needs and buying processes, but we lacked both the methodology and expertise to navigate complex, high-value deals. The co-founder recognized this gap was limiting our market potential and brought me on to solve it. I took a systematic approach to building out the enterprise sales motion from the ground up. I developed a qualification framework specifically designed for enterprise deals, ensuring we focused our efforts on opportunities with the greatest potential. I then created a comprehensive sales playbook that included objection handling tailored to the unique concerns of larger accounts. The most impactful initiative was building an ROI model that transformed how we positioned Retain's value. This model allowed sales teams to clearly demonstrate the expected return compared to costs, helping prospects see Retain as a net positive investment rather than just an upfront expense. Since most companies don't have dedicated budget for a tool like Retain, showing them where they could reallocate spend from other areas—while simultaneously demonstrating positive ROI—made the purchase decision significantly more compelling. The results were dramatic. In less than 8 months, we increased average deal size from under $6K to approximately $30K—a 5x improvement. The ROI model proved to be the game-changer, fundamentally shifting how enterprise prospects evaluated our solution and enabling us to close dramatically larger deals with greater confidence and efficiency.
Cofounded and Scaled ProfitWell to 37,000 Customers and $200M Acquisition
I cofounded ProfitWell to address a critical gap in the subscription business market. What began as Price Intelligently, a price optimization platform, evolved into a comprehensive platform serving any subscription business. We identified an opportunity to help companies optimize their pricing strategies, reduce churn through intelligent dunning, and gain actionable insights from their subscription metrics and challenges that were fragmented across multiple tools and vendors. As Chief Revenue Officer, I built our go-to-market strategy from the ground up. The cornerstone of our approach was a freemium model that allowed us to scale rapidly and demonstrate value before asking for payment. This strategy enabled us to reach thousands of users organically while building credibility in the market. I also led the sales organization and personally closed our largest enterprise deals, which validated our paid product offerings and proved that companies would invest significantly in solving their pricing and retention challenges. We scaled ProfitWell to 37,000 customers across our product suite, which included our pricing intelligence platform, Retain (our credit card dunning product), and our free subscription metrics tool. In 2022, Paddle acquired ProfitWell for $200 million a particularly strong return given we had no external investors. The acquisition enabled Paddle to integrate our pricing intelligence and retention tools into their payments platform, creating a more comprehensive, end-to-end solution for subscription businesses and validating the strategic value we'd built in the market.
Launched Credit Card Dunning Product That Generated $5M ARR in Two Years
SaaS and subscription companies were losing 20-30% of their monthly recurring revenue to failed payments—a massive problem causing involuntary churn. Existing dunning solutions required significant upfront fees, making the ROI unclear and adoption difficult for many companies. At the time, credit card dunning was either non-existent or managed through basic payment gateways like Stripe, but these solutions barely moved the needle on recovery rates. I saw an opportunity to solve this widespread problem with a fundamentally different, risk-free business model. I led the product launch by building a demo environment and creating a compelling pitch deck that emphasized our zero upfront cost model. To remove any remaining hesitation, we offered customers a money-back guarantee. Once we validated the offering with early adopters, I scaled our outbound sales motion, coordinating with Brittni and John to handle different customer segments effectively. We worked closely with key early stakeholders including Neel, Patrick Campbell, Eric Yu, Facundo Chamut, and Michael Cox to refine the product and go-to-market approach. Over the course of two years, we signed up hundreds of customers and generated roughly $5 million in annual recurring revenue. The risk-free model proved to be a game-changer, allowing subscription companies to recover significant revenue from failed payments without the barrier of upfront investment.
Launched Viral ASMR Campaign for DTC Show, Driving 60+ Comments and Thousands of Impressions
We were launching a new show aimed at DTC subscription box marketers who cared deeply about retention strategies. The challenge was breaking through the noise in a crowded space and creating a campaign that would genuinely stand out and drive attention to the show among this specific audience. I recognized that our target audience—DTC marketers—were chronically online and early adopters of emerging trends. At the time, ASMR content was exploding on Instagram and YouTube, but hadn't yet been widely adopted in B2B marketing. I saw an opportunity to leverage this trend in an unexpected way. Rather than creating a standard "here's the show" recap-style video, I conceptualized and produced an ASMR-style teaser trailer that unboxed products from our first season. This creative approach was designed to stop the scroll and spark conversation among our hyper-engaged target audience. The campaign delivered exceptional results. Our launch post on the CEO's LinkedIn generated over 60 comments, 150 reactions, and tens of thousands of impressions. More importantly, the comments came from exactly the people we were trying to reach in the DTC space, and they specifically called out the creativity of the launch. The campaign successfully positioned the show as innovative and worth paying attention to, creating the kind of buzz and authentic engagement that standard promotional content rarely achieves in the B2B space.
Scaled Pricing Framework to Serve Hundreds of Clients with Measurable Revenue Impact
Built and co-ran a pricing practice from the ground up over 10 years with 200+ projects. Worked with companies like Canva, Intercom, Blue Bottle Coffee, and many more. Over ten years as cofounder of ProfitWell I built and led a pricing advisory practice that served hundreds of subscription businesses. That meant recruiting and managing a team of pricing strategists, analysts, and working with the team of much smarter people to build the methodology we used across every engagement, and personally driving projects for some of the most prominent SaaS companies in the world...from early-stage teams pricing a product for the first time to post-IPO orgs overhauling entire packaging architectures. Every project touched real revenue.
Ran Recur Boston: ProfitWell’s flagship conference, built to compete with SaaStr and SaaStock by going the opposite direction.
In 2018, I joined ProfitWell as Events Manager, hired to build out their events and experiences program. The first big thing I built was Recur Boston, our flagship conference. At the time this was peak SaaS and in terms of events, SaaStr and SaaStock were the giants of the space. They were massive, sprawling events with sponsors, exhibition halls, ten tracks running at once, ten happy hours a day, etc. We sponsored and loved those events, but when it came to our own thing we knew we’d never outspend them. So with Recur Boston we knew we needed to go in the opposite direction to compete. We decided on a purposely small group of two hundred attendees, VP and exec level, one day, one track, one stage, in our home city, Boston. No exhibition hall. No pay-to-speak. We led with stellar content and made every other decision in service of that. We also knew the power of brand, and that for a start-up, perception is key. We understood that if we held a conference that was incredibly well done people would assume we were more established. The quick Recur Boston stats: - 200 or fewer attendees, exec level, one track - Top speakers including Rand Fishkin, Dan Martell, David Cancel, and Katie Burke with extra long 45-60 min slots to go deep on a topic. Speakers really needed to hold their own to speak for that duration. - Recouped event cost in ticket sales alone - Closed revenue more than 5x event cost - No exhibition hall, no paid speaker slots - Built and run inside a bootstrapped company The messy middle parts: 1. I came to ProfitWell from an events agency. I was great at my job, but I was trained to be a gun for hire. I was used to creating and presenting three options to a client and recommend the right one. The client made the call and then I executed. The first time I did this at ProfitWell, our CEO Patrick stopped me mid-recommendation and asked me "What do you think the right call is?" I told him. and his response was just "Okay, do it." I was the perfect person to own Recur at that time because in that moment I realized I had years of stuff that I wanted to do that I could just execute. I knew the right call and it was incredible to simply do it. 2. The standard playbook for a conference is theme-first. You decide what the show is about, then find speakers who fit. We went a different direction. We asked speakers what they were excited about, what they were working on, what they couldn’t shut up about with their teams. The themes then came out of the speakers, not the other way around. Speakers were pumped and often tried out new talks with us first. This was a key way for us to put content first, earn the speakers trust, and ensure that what our attendees were hearing was fresh instead of forced. 3. One thing I am unyielding on is the perfection of small stuff with events. Those small things can seem trivial, but when you add them up they can completely make or break the experience. It's knowing where to park or walk, wifi that connects, good lighting, water before you need to ask. It’s a thousand small things going right, all at once, that elevate the event. I would be remiss in the telling of this story if I did not mention my talented counterpart Dan Callahan. Dan was the Creative Director at ProfitWell, and was the brain behind much of the brand. He designed and I had the honor of bringing those designs into the physical world. I'll end with this - Recur became one of the things ProfitWell was known for and one of the best received and reviewed events in SaaS at the time. The brand we built around it punched at the level of competitors 10x our size. That positioning was a piece of ProfitWell's growth and ultimately acquisition.
Built Custom Segmentation Engine on Elasticsearch for High-Volume Subscription Analytics
ProfitWell's core offering was billing analytics for SaaS companies, and one of our most requested features was to be able to segment a company's SaaS metrics (e.g. MRR, retention rate, growth rate, etc.) by all of the various attributes of a company's customer base (e.g. demographics, signup date, location, lifetime spend, current plan, etc.). This proved challenging given the volume of data we were processing, and the fact that that these metrics needed to be computed in a HTTP request lifecycle, since we couldn't be sure what exact query the customer would run. I designed and implemented a segmentation engine that would (1) automatically and continuously synchronize with our primary, source-of-truth, databases, (2) calculate, on the fly, the most important SaaS metrics given a filter of customer attributes, and (3) scaled it up to handle ProfitWell's largest customers at a reasonable cost (since we were offering the metrics platform for free).
SaaS Event Support
Was frequently the "product guy" helping our enterprise sales teams at PW with on the ground support at events like SaaStock, SaaStr to provide product context to prospects. Would serve as a technical touch point to high priority leads and represent the company at VIP events.
Supported due diligence leading to $200M acquisition
ProfitWell got acquired by Paddle for $200M. Leading up to this transaction, I was on a small team assisting the CEO and legal teams with various aspects of due diligence for the PW Metrics and Retain products.
Implemented NPS
We had 30k+ free users of PW Metrics and we wanted a pulse for how customers were liking our platform. However rather than just getting a score for NPS, we wanted to make it actionable and a feedback loop to improve the product. I implemented a dynamic follow up system to 1) seek feedback from users who scored 1-8 NPS, while 2) asked 9 and 10s to leave a review for us on G2 Crowd followed by sending them a Swag Pack to make them champions of our products. We averaged an NPS of ~60 over the years.
Implemented product analytics stack
While Product Lead for PW Metrics, implemented the following tools to better understand how customers were using our product: -FullStory -MixPanel -LogRocket -Segment -Appcues
Implemented PLG motion from scratch leading to 120% NRR
While Product Lead for Retain, I developed the PLG motion to drive expansionary revenue from our customers. This included tiered usage based billing for self serve customers, and high touch account management for enterprise customers (ACVs > 100k/year). I personally played CSM for our top 1% of customers and closed contracts exceeding 250k/ year. We sustained 120% NRR and <2% revenue churn for ~2 years leading up to the Paddle acquisition. I have fun stories of trying to implement revenue quotas for PMs :)
Improved month 2 retention by 20%
While PM of PW Metrics, I implemented AppCues for user onboarding. This included creating a welcome tour that highlighted aspects of the platform, creating a knowledge base for FAQs, and overhauling email campaigns that activate new users. After 6 months, retention for new cohorts improved by an absolute 20%.
Migrated ProfitWell Infrastructure from Heroku to Kubernetes on AWS
When I joined ProfitWell, the infrastructure was running on Heroku instances—a setup that worked for getting started but had become a significant constraint on our growth. Engineers were manually pushing code from their local machines directly to production without any CI validation, which introduced deployment risk. Heroku's IaaS costs were substantially higher than running our own VMs on AWS, and we were rapidly approaching their hard limit of 10 instances per service on our main processing workload. For a bootstrapped company planning to scale, this wasn't sustainable. My mandate was clear: support 10x growth in data processing volume while keeping infrastructure costs in check, and accomplish it without downtime or expanding the ops team. I executed a carefully staged migration to eliminate these bottlenecks. I started by provisioning a parallel Kubernetes cluster in AWS and building Terraform modules to codify each service's infrastructure. Next, I established CI/CD pipelines in CircleCI that automated Docker image builds and deployments via Helm charts—replacing the risky manual process with a reliable merge-and-deploy workflow. To minimize risk, I migrated services incrementally, beginning with lower-priority background jobs before tackling the customer-facing API. The results were immediate and measurable. We cut infrastructure costs by roughly 20% right away while completely removing the scaling ceiling that Heroku had imposed. The new Kubernetes environment could scale horizontally to meet our 10x growth target without architectural rewrites. Just as importantly, the CI/CD automation freed engineers from manual deployment toil and dramatically reduced deployment risk, allowing the team to ship faster and with greater confidence. This foundation enabled ProfitWell to scale efficiently without ballooning headcount or cloud spend.
SaaStr Sponsorship 2018-2020
Built the experiential growth strategy that enabled ProfitWell to procure the most leads out of any sponsor (at any level) at the largest industry events (SaaStr & SaaStock)