Task at Hand
Doug's Climb
Before the hypergrowth climbs, there were those with no trail markers. At Endeca and Bit9/Carbon Black, there was no budget line for what we were selling. No RFP waiting. No category yet defined. Success meant going deep enough into a customer's world to discover their own problem — and then helping them build the case for change together. That's where the foundation of value selling was forged. In the field, out of necessity.
Splunk
$200M to $2B+ ARR
Users loved the product, but CIOs called it too expensive. The issue wasn't pricing — it was that customers couldn't see or quantify the value they were already getting. A classic value gap, showing up in the field before anyone in the executive suite had named it.
We went deep into customer discovery — mapping business processes, uncovering latent pain points, and translating a highly technical PLG motion into executive-level value conversations. Then invented and industrialized the system: documented the patterns, built a delta force team of experts, and created the tools and automation to scale it across the entire field.
The result: a 5x greater win rate when the model was engaged. And a complete transformation from bottom-up technical selling to top-down executive buying.
Databricks
$100M to $1B ARR in 3 years
Databricks required a different version of the same discipline — rebuilt this time for a consumption model where value visibility isn't a sales tool, it's an existential requirement. Customers would land at low cost and then face a pivotal moment: commit production workloads and spend significantly more, or walk away. If they couldn't see what they were getting, they'd stop consuming.
We rebuilt the Value Acceleration system from the ground up — bringing McKinsey-style business cases into the land, adopt, expand, and renew motion. The result: a 5.8x win rate when the team engaged. From there we layered in a PS investment model — scoping technical gaps account by account, selectively deploying resources into high-consumption potential accounts. Those customers grew 4x faster than the rest of the base. Then we built an executive engagement capability — pulling the data and AI conversation out of technical teams and into the C-suite for the first time.
Three functions. One compounding system. During that run, Databricks grew 100% per year — from $100M to $1B ARR in three years.
Datadog
$1.5B to $2.5B+ ARR
Datadog was a different kind of climb. The work was less about building new functions and more about making a complex, scaling GTM machine run better — and running it differently.
That meant transforming the new logo motion to target the highest-potential accounts: acquiring third-party data, building territory-based TAM models, and restructuring AE and SDR compensation to drive focus where it mattered most. It meant creating standardized playbooks — territory planning, account planning, white space analysis — so that good judgment could scale across a global field organization. And it meant hosting the first-ever global GTM leadership meeting, which became a twice-yearly institution, and executing SKO2024 around the theme of One Datadog.
Our Experience
Harness
Building the GTM Engine from the Ground Up
Harness was the most complete build of the four climbs. Not inheriting a machine — constructing one. Six functions, rebuilt or created from scratch: Field Enablement, Revenue Operations & Strategy, Sales Development, Strategic Advisory (Value and Domain specialists), Business Development, and AI integration across the entire GTM motion.
The enablement model started as just-in-time delivery — giving AEs what they needed, when they needed it, at the right moment in their tenure. It's been revised twice and is now evolving toward something closer to what Alpha School pioneered in education: AI-powered, personalized, mastery-based learning that compresses time without sacrificing depth. The goal isn't a longer program. It's a smarter one.
The Strategic Advisory function — built around a four-part charter — became a driving force for GTM innovation in the field. The SDR team reached a milestone most organizations talk about but rarely hit: promoting quarterly SDRs into AE roles from within.
And then there's the Sales Efficiency Summit — an annual event where field data, surveys, and interviews get synthesized in a McKinsey-style working session to identify the highest-leverage Productivity Improvement Initiatives. The kind of thing that looks simple from the outside and is brutally rigorous from the inside.
RESULTS
• 43% increase in sales productivity
• 50% reduction in AE ramp time
• 5x win rate when Strategic Advisory engages
• 25% relative increase in Harness growth rate — with another 20% forecasted
PTC
It rarely announces itself. One quarter the pipeline looks healthy. Then something shifts — win rates soften, ramp times stretch, the enterprise deals that were supposed to land don't. Leadership starts by asking questions.
This isn't a talent problem. It's not a product problem. It's a stage problem.
Every meaningful growth inflection demands a different GTM focus. Sometimes that's a slight adjustment — a coverage tweak, a new value conversation, a sharpened ICP. Sometimes it's a more significant move. But the companies that stall are almost always running the last-stage playbook at the new stage's elevation.
Underneath most of it is a value gap — a disconnect between your team's conviction about what your product does and what customers understand and realize. Unless you are paying attention, that gap widens at every stage. Most companies don't know it's there until the numbers tell them something is wrong. That slows you down and puts your company at risk.
Let's help you figure out what to do about it.Task at Hand
Wendy's Climb
Before the operating roles, there was the methodology. At Strategic Pricing Group — now part of Deloitte — Wendy spent six years developing value-based pricing and selling frameworks for Fortune 500 companies launching innovative products, including AT&T (voice recognition), Corning (fiberoptics), and Microsoft (e-learning). There was no template for what she was building. The discipline had to be invented from first principles, client by client, industry by industry. That’s where the foundation was forged: the conviction that pricing isn’t a number — it’s a signal of value, and only works when the whole commercial architecture is aligned behind it.
We don't just hand you a map.
Most advisors operate from a distance. They assess, recommend, and move on — leaving your team to figure out the implementation. That's not how you reach your summit.
A sherpa doesn't watch from base camp. They're on the rope with you — reading the terrain, adjusting the route, carrying weight when the altitude bites. That's how we work.
Value Sherpas brings operator-grade experience to every engagement. We've held the roles your leaders hold. We've built the functions your team is trying to scale. That means we don't just diagnose. We get in and do the work — building with you, alongside your team, embedded in your reality, your customers, your competitors, accountable to outcomes.
See Our StorySplunk
It rarely announces itself. One quarter the pipeline looks healthy. Then something shifts — win rates soften, ramp times stretch, the enterprise deals that were supposed to land don't. Leadership starts by asking questions.
This isn't a talent problem. It's not a product problem. It's a stage problem.
Every meaningful growth inflection demands a different GTM focus. Sometimes that's a slight adjustment — a coverage tweak, a new value conversation, a sharpened ICP. Sometimes it's a more significant move. But the companies that stall are almost always running the last-stage playbook at the new stage's elevation.
Underneath most of it is a value gap — a disconnect between your team's conviction about what your product does and what customers understand and realize. Unless you are paying attention, that gap widens at every stage. Most companies don't know it's there until the numbers tell them something is wrong. That slows you down and puts your company at risk.
Let's help you figure out what to do about it.