The Problem-First Playbook
Ross Sylvester, Co-Founder & CEO, Adrata | Feb 2026 | ~10 min read
In 2015, Jessica Lin and Jonathan Lehr launched Work-Bench with $10 million and a thesis that most venture capitalists had backwards.
The standard model: find a promising startup, then figure out who would buy the product. Lin and Lehr flipped it. They started with Fortune 500 CIOs. Not to pitch them. To listen to them. To catalog every problem they couldn't solve with existing tools. And then -- only then -- to find or fund the startups building solutions to those specific problems.
A decade later, Work-Bench closed their fourth fund at $160 million. Their portfolio includes Socure, now valued at $4.5 billion, which they introduced to Bank of America as its first major customer. Not because they had a better pitch deck. Because they already knew Bank of America's problem.
This is not a venture capital essay. This is about a methodology that the best CROs in enterprise sales should steal -- and most have never heard of.
The Model
The problem-first approach has been independently discovered by at least six major investment organizations. The pattern is identical every time:
Insight Partners runs an 18-month CIO Council embedding 15+ CIOs from the Global 2000 directly into their investment process. Since 2022, the program has produced nearly 600 high-impact connections between Council Members and portfolio companies -- pilot programs, commercial agreements, corporate venture investments, and strategic product feedback loops. The 2025 cohort includes CIOs from Intel, Procter & Gamble, CIBC, Lego Group, and Stanley Black & Decker.
Trace3 tracks approximately 500 startups at any given time through an in-house Innovation Research Team. When a CIO presents a problem, Trace3 lines up previously vetted startups in a "speed-dating" briefing format -- 13+ startups in a single session, each getting 15-30 minutes. "The program helps define what my portfolio should include in two to three years," said Niel Nickolaisen, CTO at O.C. Tanner.
Silicon Valley CISO Investments (SVCI) assembled 60+ Chief Information Security Officers into an angel syndicate. Members evaluate startups based on operational pain they experience daily -- not market projections or competitive analyses. Their portfolio includes Drata, Island, Orca, and Traceable. They don't ask for board seats. They build.
Andrew Ng's AI Fund has raised $370 million+ to build approximately one new AI company per month. Corporate partners identify market gaps in their industries. The AI Fund assesses what technology can and cannot do, recruits CEOs, and builds alongside the team. "I'm personally involved in every single company we build," Ng has said. "We write code with our portfolio company."
The thread connecting all of them: they start with the problem, not the solution.
Why This Matters for Revenue Leaders
Replace "CIO" with "buyer." Replace "startup" with "your solution." The methodology maps directly.
| What the Best Investors Do | What the Best Revenue Teams Should Do |
|---|---|
| Build curated executive communities | Build account-based relationship intelligence |
| Ask "what can't you solve?" | Lead with discovery, not pitch |
| Catalog problems across a portfolio | Map unresolved outcomes across accounts |
| Validate problems across multiple execs | Validate pain across the buying committee |
| Match solutions to verified problems | Position your product against verified outcomes |
| Close the loop with post-investment support | Deliver measurable post-sale value |
The parallel is structural. And yet, most sales organizations operate the exact opposite way: they start with their product, build a pitch, and then go looking for someone who might want it.
Josh Wolfe of Lux Capital captures the right starting question in two words: "What sucks?"
The Single Person at the C-Suite
Here is where the model gets specific for CROs.
Every enterprise has a finite number of people who can articulate the organization's biggest unresolved problems. Not the departmental annoyances. Not the feature requests. The problems that cost the company real money -- the ones keeping the executive team up at night.
Work-Bench found their CIOs at Fortune 500 headquarters clustered in New York. Insight Partners curates them through a formal application process. SVCI recruits through personal invitation and vetting.
For a revenue team, the question is simpler: who is the single person in the buyer's organization who knows the unresolved problem worth $1M+ to fix?
This person has three characteristics:
1. Authority over the budget. They can approve or influence spend without needing to build consensus from scratch. In Work-Bench's model, these are CIOs -- people who control hundreds of millions in IT spend. In your deal, this is the economic buyer who controls the budget line where your solution lives.
2. Awareness of the gap. They know what isn't working. Not vaguely -- specifically. "We lose 30% of our pipeline because we don't know who the actual decision-maker is." "Our reps spend 4 hours a day on research that should take 15 minutes." "We've missed forecast 3 quarters in a row because deal intelligence is scattered across Slack, email, and gut feel."
3. Willingness to act. Knowing the problem is necessary but not sufficient. The person you need is the one who has tried to fix it before, failed, and is willing to try again with a better approach. This is why SVCI works -- every CISO in the syndicate has personally wrestled with the problems their portfolio companies solve. They don't need to be convinced the problem exists. They need to be convinced this solution is different.
The intersection of authority, awareness, and willingness is your target. In a typical enterprise with 15,000 employees, there are maybe 5-10 people who meet all three criteria for any given solution category. Finding them is the most valuable activity in enterprise sales.
How Many Relationships Do They Have?
The problem-first model only works at scale if the relationship layer is real. Work-Bench built a community of 10,000+ enterprise technology professionals through the NY Enterprise Technology Meetup. Insight Partners maintains a network of 50+ CIO Council alumni across four cohorts. SVCI has 60+ CISOs who meet twice quarterly.
The relationship is not transactional. It's structural. These executives participate because they get value independent of any specific deal: peer insights, early access to innovation, strategic visibility.
For revenue teams, the same principle applies. The number of genuine C-suite relationships your organization maintains -- not contacts in a CRM, not LinkedIn connections, but actual relationships where you understand their unresolved problems -- is your leading indicator of pipeline quality.
Most sales organizations measure the wrong thing. They count touches, activities, meetings booked. But the metric that predicts revenue is: how many C-suite executives could you call right now who would take the meeting because they trust you to bring something worth their time?
If the answer is fewer than 20, you don't have a pipeline problem. You have a relationship problem.
Mapping Unresolved Problems to Revenue
The venture firms that use this model don't just listen. They systematically catalog what they hear.
Trace3's Innovation Research Team tracks 500 startups organized by problem category. When a CIO says "I can't get visibility into my cloud security posture," Trace3 already has 4-5 vetted startups that address that exact issue. The matching happens in real time because the catalog was built in advance.
For revenue teams, this means building an outcomes library -- a structured inventory of the unresolved problems your solution addresses, mapped to the specific executive titles who experience them, the specific metrics they care about, and the specific proof points (case studies, data, references) that demonstrate resolution.
This is not a battle card. Battle cards are about your competitors. An outcomes library is about your buyers' problems.
Structure it like this:
- Unresolved Problem: CROs can't see who the real decision-maker is until it's too late
- Who Feels It: VP Sales, CRO, Head of Revenue Operations
- What It Costs: 22% lower win rates on deals where the economic buyer isn't identified by Stage 2
- What Resolution Looks Like: Automated buyer group mapping that identifies the economic buyer, champion, and blockers from engagement data
- Proof: [specific customer, specific result, specific timeframe]
Build 10-15 of these. Your discovery calls become problem-matching conversations, not feature demonstrations. Your reps stop pitching and start diagnosing. Your deals move faster because the buyer recognizes that you understand their problem better than they've articulated it themselves.
The Compounding Effect
Venture firms keep reinventing this model independently. The reason: it compounds.
Work-Bench's first fund was $10 million. By the time they raised their fourth, it was $160 million. Not because they got better at picking startups. Because their relationship network deepened, their problem catalog expanded, and their pattern recognition improved. Each successful match created a reference that attracted more executives to the community, which surfaced more problems, which attracted better solutions.
For revenue teams, the same flywheel operates:
- Deep discovery surfaces the buyer's real problem
- Precise matching demonstrates competence
- Successful implementation creates a reference
- The reference attracts similar executives
- Similar executives bring similar problems
- Pattern recognition accelerates matching
- Back to step 1, but faster
This is why the best enterprise sales teams are not organized around products or territories. They're organized around problem categories. The rep who has solved the "we can't forecast accurately" problem twelve times is exponentially more effective than a generalist -- not because they're a better seller, but because they've built the problem-first catalog that lets them match immediately.
The Revenue Organization as Venture Fund
The final insight from the problem-first investors is the most important.
Andrew Ng's AI Fund doesn't just invest. It builds alongside the team. "Our team is very AI-enabled... everyone knows how to code. We're literally all builders." SVCI members don't just write checks. They provide product strategy feedback, pricing guidance, and operational expertise. Work-Bench doesn't just wire money. They make customer introductions that determine whether a company succeeds or fails at the zero-to-one stage.
The common thread: they don't stand apart from the value creation. They are part of it.
The best revenue organizations operate the same way. They don't just sell a product and walk away. They co-create the outcome with the buyer. The rep who understands the buyer's problem deeply enough to reshape the implementation plan. The customer success manager who identifies an expansion opportunity the buyer hadn't considered. The executive sponsor who connects two customers facing similar challenges.
This is what separates transactional selling from enterprise selling. And it's what makes the problem-first playbook so durable. When your starting point is the buyer's unresolved problem -- genuinely understood, carefully cataloged, precisely matched -- the relationship doesn't end at close. It compounds.
The venture investors figured this out. The revenue leaders who adopt the same methodology will outperform those who don't. Not by a little. By the same margin that Work-Bench's returns exceed the average seed fund.
Start with the problem. Everything else follows.