Hiring PricingMonkey's First Product Manager
From Founder Bottleneck to Product Engine: The Pricing Monkey Story
How we helped a bootstrapped fintech SaaS scale their product function and reclaim 30% of founder time lost to product chaos.
“The difference is night and day, really. We’ve hired a world-class product manager who we’re really happy with. Before we worked with Nick, we didn’t know what good looks like, we were drowning in work and delays and were struggling to find candidates we could get excited about” - Alec Clements, CEO
The Founder’s Dilemma
PricingMonkey is an innovative tool for pricing and analyzing listed derivatives that’s seen explosive growth over the last 18 months after 7 years of steady growth. Their market-leading platform serves top investment banks, brokers, asset managers, and hedge fund traders, processing over 50,000 trades daily across 500+ products.
Their B2B SaaS pricing-ops platform with sophisticated UI was winning customers and driving record year-over-year revenue growth, offering features like intuitive trade entry, effortless charting, and a powerful spreadsheet interface. But behind the scenes, the five-founder team was drowning.
“We felt like we were drowning in work… delays were creeping in, and we still had 80% of our product vision left to build,” recalls Alec Clements, CEO of PricingMonkey.
The 15-person team (5 founders/executives and 10 engineers) faced a classic scaling problem:
- Founders spent 30-40% of their time prioritizing features, writing specs, and chasing work (~22-30 hours/week across the founding team)
- Feature delivery was slowing despite increasing customer demand from portfolio managers, brokers, market makers, and risk managers
- Four months of traditional recruiting yielded plenty of candidates, but zero hires — the team was split on what “good” meant for their first PM
- Feature delivery was slowing despite increasing customer demand.
- Four months of traditional recruiting yielded plenty of candidates, but zero hires — the team was split on what “good” meant for their first PM.
- They needed someone to own the product process and free the founders to focus on growth.
Breaking the Cycle
As an experienced founder and Chief Product Officer who’s interviewed thousands of product managers, Nick helped Pricing Monkey find the gem for their next growth phase.
The engagement: Half a day/week for 16 weeks at a fixed monthly fee.
We tackled this challenge with a three-part approach:
1. Redefining the Role
Most hiring fails before it begins due to unclear role definitions. We conducted deep product walkthroughs and focused founder interviews to uncover what success looks like.
The outcome wasn’t “hire a PM”—it was “own prioritization and specs so founders can focus on growth.” This clarity allowed us to create a tiered requirements list (Must-Have/Nice-to-Have/Wishlist) that reflected Pricing Monkey’s needs.
What we uncovered: The founders weren’t aligned on whether domain expertise (derivatives pricing) trumped product methodology. After a workshop, we defined success metrics for the role: taking ownership of the existing product and driving its ARR and engagement targets - with specific metrics.
2. Building a Hiring System, Not Just Filling a Seat
The system we built was about:
- Getting clear on this role’s responsibilities.
- Introducing a written task as Phase I
- Written screener asking 3 simple questions to identify high-quality candidates and filter down from many options to a small handful.
- We went deep on that small handful, showing them product demos, getting their feedback, and bringing them into workshops quickly.
This approach eliminated 80% of unqualified applicants before the first call, improving the signal-to-noise ratio.
The system in action: Our screener included the question: “How would you prioritize features for a derivatives pricing platform with both buy-side and sell-side users?” Top candidates demonstrated domain awareness and prioritization frameworks. One standout response began:
“I’d segment feature requests by user type and map them to revenue impact. For buy-side analysts, optimization features drive retention, while for sell-side, it’s about coverage breadth…”
This filter eliminated 80% of applicants before the first call, improving the signal-to-noise ratio. The approach takes 15 minutes per candidate but saved the founders 40 hours of interviews.
3. Targeted Sourcing
With a clear spec, we:
- Built a repeatable sourcing funnel targeting product leaders with fintech experience.
- Created a scorecard system for all team members.
- Implemented weekly funnel reviews to refine our approach.
The Transformation
The results speak for themselves:
| Before Working With Nick | After 16 Weeks |
|---|---|
| 0 viable PMs after 4 months | Signed preferred PM candidate |
| Founders spending 30-40% of time on product admin | 20-30% founder time freed for strategy and growth |
| Ad-hoc, inconsistent interviews | Repeatable 4-round process for all technical hires |
| Misalignment on role requirements | Clear, outcome-based metrics and interview questions |
“The difference is night and day,” says Alec. “We follow the format you introduced for every hire now. You seemed on it—detailed feedback within hours and a framework that works.”
The Real Impact
For Pricing Monkey, this wasn’t just about filling a position. The transformation will deliver:
- Accelerated Feature Velocity: Clearing the bottleneck delaying new functionality crucial to expanding beyond their current market niche.
- Organisational Scalability: Establishing a dedicated product function ahead of future growth
- Hiring Blueprint: Reducing risk and cycle time for future specialist hires
The new Product Manager starts in May 2025, allowing the founders to focus on strategy while maintaining product excellence. The team plans to apply the same process to hire a Product Designer in Q3 2025.
Are Your Founders Trapped in the Day-to-Day?
If your technical founders are spending too much time on execution rather than strategy, you’re not alone. The transition from founder-led product development to a scalable product organization is a challenging inflection point for deep tech startups.
Book a 30-minute fit call to plan your 90-day hiring sprint and eliminate the founder bottleneck.
Related Articles on Hiring Product Leaders
If you’re working on hiring product managers, check out these related articles:
- The Founder’s Guide to Senior Hires - A comprehensive framework for identifying, attracting, and hiring senior leaders
- How to hire a product manager in a tight labour market
- How to interview your startup’s first product manager
- What to look for in your first product manager
- What product managers want from their jobs
- What’s the right amount of ownership for startup PMs to have
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