Tom Dunlop had to manually review 500 contracts during an acquisition. Then his CFO asked him to go back and check one more clause across all 500. That pain drove him to build Summize, a contract management platform now doing late 7-figure ARR.
But finding the right first customers took 18 months of chasing the wrong ones. Tom sold to law firms, in-house teams, companies of every size – riding the dopamine hit of “happy ears” instead of focusing on who actually converted. The breakthrough came when he stopped casting a wide net and started targeting a specific persona with a specific pain.
Tom Dunlop is co-founder and CEO of Summize, a contract lifecycle management (CLM) platform that helps companies create, review, and manage contracts.
In 2019, Tom was working as an in-house lawyer for a tech company. During an acquisition, he had to manually review 500 contracts – a painful task that got worse when he had to repeat the entire process just to check one additional clause.
This frustrating experience led him to partner with a software engineer to build a prototype that could automatically create contract summaries. After getting positive feedback from potential customers, they raised 250K to build the product. Then COVID hit right as they were launching.
But what seemed like terrible timing became an opportunity. Companies scrambled to understand their contract obligations during the crisis, and Summize found its first customers among catering and events businesses that needed to understand cancellation clauses overnight.
Still, the path to repeatable growth was unclear. Tom spent the next 18 months chasing any customer he could find – law firms, in-house legal teams, companies of all sizes. He fell into the “happy ears” trap, where positive feedback felt like validation but never turned into deals. The breakthrough came when Summize narrowed its focus to in-house legal teams at mid-market companies and built the product to work inside tools people already used daily – Teams, Slack, Outlook, Salesforce.
Tom Dunlop grew Summize to late 7-figure ARR with 100%+ year-over-year growth by focusing on a narrow ICP and building outbound sales as the primary growth engine. The company has raised $10 million and serves customers like Revolut, Rothschild, and Miami Heat.
Today, Summize is approaching 8-figure ARR with dual headquarters in Manchester and Boston.
Key Insight
Key ideas
- Spent 18 months chasing law firms, in-house teams, and companies of all sizes before narrowing ICP - Conflicting product requests from different customer types made it impossible to build a coherent roadmap - COVID created urgent first customers among catering and events businesses needing contract clause review - PLG failed because contract review software is too complex for self-serve onboarding - Outbound became the primary growth engine only after targeting a specific persona with a specific pain📖 Chapters
00:00 Introduction and Roger Federer's 54% mindset
01:28 What Summize does and who it's for
03:11 Revenue, growth, and key customers
04:00 Total funding raised
04:12 The 500-contract pain that started it all
05:44 Building the prototype with a co-founder
06:30 Sponsor break
07:25 From prototype to real business
08:52 Raising 250K pre-seed for development
09:36 Building the MVP over six months
10:48 Going back to early believers and asking them to pay
11:23 Finding first customers during COVID
13:08 Selling pain relief during a crisis
15:19 The 18-month “happy ears” trap
18:18 How long unfocused selling lasted
19:14 Choosing in-house legal over law firms
21:09 Narrowing to specific verticals
22:24 How unfocused ICP corrupted the product roadmap
24:38 Why PLG didn't work for contract software
27:08 Free trials and published pricing experiments
27:54 Events as a growth channel – what went wrong first
30:51 How events became the best ROI channel
32:06 Breaking into the US market
34:46 Summize's biggest product differentiator
35:54 Lightning round
🔑 Key Lessons
- 🎯 **Stop chasing "happy ears" when finding first customers:** Summize spent 18 months reacting to any positive feedback instead of tracking which customer type actually converted fastest. Positive interest is not the same as purchase intent. - 📉 **An unfocused ICP corrupts your product roadmap:** Law firms wanted client portals while in-house teams wanted Salesforce integrations. Conflicting requests from incompatible customers made it impossible to build a coherent product. - 🔄 **Use crisis to find your first customers:** COVID forced catering and events businesses to urgently review contract clauses. Summize targeted companies with the most immediate pain rather than the most obvious market. - 🛠️ **PLG is not right for every SaaS product:** Despite being told they were "quick and easy," contract review software was too complex for self-serve. Summize abandoned PLG after 3-4 months and returned to sales-led growth. - 🤝 **Your background is a cheat code for selling to your first customers:** As a former in-house lawyer, Tom could immediately articulate the exact daily pain his prospects faced. Domain expertise shortened sales cycles dramatically. - 🏢 **Different markets need different scripts:** In the US, buyers already understood CLM and wanted differentiation. In the UK, Summize still had to educate prospects on the category. Same product, completely different sales conversations. - ⚡ **Work events before you attend them:** Summize flipped events from worst ROI to best ROI by getting attendee lists in advance, booking meetings before the event, and running structured follow-up sequences afterward.Show Notes
Book Recommendations
- From Impossible To Inevitable by Aaron Ross and Jason Lemkin
Episode Q&A
**How did Tom Dunlop come up with the idea for Summize?**
Tom had to manually review 500 contracts during an acquisition as an in-house lawyer. When his CFO asked him to go back and check one more clause across all 500, the pain was severe enough to build a solution.
**How did Summize find its first customers during COVID?**
COVID created urgent demand from catering and events businesses that needed to understand cancellation clauses in their contracts overnight. These companies couldn't afford outside counsel and needed an automated solution.
**Why did Summize spend 18 months chasing the wrong first customers?**
Tom fell into the “happy ears” trap where positive feedback from diverse prospects felt like validation. Every time they closed one deal in a random vertical, it gave them enough hope to keep casting a wide net instead of focusing.
**How did an unfocused ICP hurt Summize's product development?**
Law firms wanted project management and client portals while in-house teams wanted Salesforce integrations and calendar features. The conflicting roadmap requests made it impossible to build a coherent product until they picked one customer type.
**Why did product-led growth fail for Summize?**
Contract review is too complex for self-serve onboarding. Despite positive feedback about being “quick and easy,” users couldn't get value from the product without configuration and onboarding support. They abandoned PLG after 3-4 months.
**What was Summize's biggest differentiator when entering the US market?**
While US competitors had already educated the market about CLM, Summize's differentiator was embedding directly into tools like Teams, Slack, and Salesforce – so no one had to go to summize.com to get value.
**How did Tom Dunlop turn events from worst ROI to best ROI channel?**
Initially Summize chased “happy ears” at conferences without strategy. The turnaround came from getting attendee lists in advance, booking meetings before the event, and running structured follow-up sequences afterward.
**What made Summize finally narrow its target market to in-house legal teams?**
The sales team naturally gravitated toward in-house legal at mid-market companies because deals closed faster and commissions were higher. Tom's own background as an in-house lawyer gave him a “cheat code” for resonating with this persona.
**How did Summize grow from late 7-figures to approaching 8-figure ARR?**
By focusing outbound sales on specific verticals with tailored messaging – growth companies heard about removing contract bottlenecks, while operational companies heard about managing complex signed agreements. Each vertical got a different pitch.