Why Great CROs Stop Managing Numbers and Start Building Systems with Sam Costello

Business strategy & role shift (number-carrying → revenue-system ownership)

• Sam Costello’s perspective changed when moving from prior sales leadership roles to CRO: revenue becomes an output of building an “execution machine” rather than primarily driving pipeline/targets directly.
• At Harness, go-to-market “machine” priorities are:
  • Recruiting elite talent
  • Developing/enabling teams
  • Running a crisp, qualified sales process (“in command and control”)
  • Forecasting with confidence to grow toward an IPO

Company background (Harness)

• Harness positioning: “AI for everything after code”—how software artifacts reach production safely, securely, reliably, in a governed/deterministic way.
• Growth/tenure claims:
  • Joined at Series A in 2019 as the first sales leader under CRO Jason Eubanks
  • Helped grow from < $1M ARR to $100M ARR in 5 years
  • Continued moving through senior sales leadership seats to become CRO

CRO operating rhythm (where time goes)

Sam estimates time allocation as CRO:

• ~40% recruiting (business needs heads fast; high standards for “excellence”)
• ~20% customer-facing selling
• Remaining time focused on enablement and execution governance:
  • boot camps / enablement
  • metric reviews (“medic reviews”)
  • ensuring the sales process is followed and performing

Enablement framework: centralized + regional training

• Training buckets:
  • Corporate/company-wide enablement for new products & industry updates
  • Regional enablement led by “second lines” (called Chief Enablement Officers) who customize training to the needs of their region/team (different needs for ramping reps vs senior reps)
• Process expectation:
  • Second lines build or source content based on local pulse, often via internal SMEs or outside speakers.

Sales playbook: Harness “Duplo” process (champions first)

• Core framework: Duplo sales process
  • “Find a champion and then do everything else.”
• Required sequencing:
  1. Identify/build champion(s)
  2. Confirm there’s real pain the company cares about
  3. Reach the economic buyer (EB)
  4. Build confidence through business case + proof

“Big deal” ingredient trap (pricing-scale follows confidence, not pitch)

• Warning against a common failure mode:
  • Sellers get excited about pain + champion, then pitch toward a large transaction prematurely.
• Instead, a large deal emerges when:
  • pain is important to the organization,
  • champion(s) build confidence,
  • EB is engaged, and
  • customer pulls you into scaling via confidence.

Champion sizing mismatch (when deal size changes, champion must evolve)

• Another failure mode:
  • Champion created for a smaller initial deal (e.g., $500k) but reps attempt to scale into a much larger deal (e.g., $5M) without re-qualifying/upgrading the champion.
• Result:
  • stuck in late-stage decision criteria, papering, and governance because the right influence isn’t present.

Technical validation & Proof of Value (POV) system

• Harness sells a highly technical platform consisting of ~14 products, requiring multi-stakeholder validation.

Typical POV structure (multi-threaded buying)

Deals often need 2–3 champions / technical mindshare across:

• platform tooling team
• developer engineering consuming team
• security team with governance/policy requirements

POV format evolution

• Early stage:
  • POVs often required installing into customer environment
• Mature stage:
  • now ~30–40% is workshop-style (not installed)
  • ~60% includes installation to prove it works in their environment

POV governance / qualification thresholds

• Buyers require outcomes they can trust in their environment.
• Harness enforces strict POV criteria:
  • champion exists (ideally multiple) + mindshare coverage
  • POV criteria are defined and highly differentiated
  • POV success criteria align with the EB
  • SE leader signs off globally
  • CRO signs off on POVs

Go/no-go process for POVs

• POVs run only when internal qualification gates are met.
• Emotional “deal-close” proximity is treated as a risk—leaders must maintain radical commitment to the process or escalate deviations (to Carlos/Sam), rather than passing them to pipeline.

Deal economics: POVs are not charged

• Harness does not charge for POVs (funded “out of pocket”) as long as they fit the process.

Land-and-expand execution (mechanics of “land”)

• Harness supports land → delight → expand:
  • Land where it makes sense
  • Ensure success
  • Expand into the right transaction
• POV is positioned as the qualification mechanism that helps justify expansion by:
  • verified technical fit
  • business-case alignment
  • multi-threaded mindshare across stakeholders

Linking technical proof to business outcomes (business-case discipline)

• Sam emphasizes a key transformation:
  • Many sellers achieve technical awareness but fail to connect to business outcomes, blocking EB engagement.
• Their method:
  • Create a business case first (may be early/incomplete, but “strong man business case”)
  • Tie POV planned proof points to that business case with metrics:
    • “the capabilities we prove in the POV tie back to the value hypothesis”
  • Ensure the economic buyer is seen before POV:
    • confirm they care about the problem
    • confirm decision criteria
    • confirm if direction changes, EB will be re-engaged

Champion deposits → give/get dynamic

• Trust is built in stages:
  • Early: education/awareness to build trust (“champion deposits”)
  • Later: move to give/get
    • champion receives needed proof/learning
    • seller receives qualification signals

MEDDIC / qualification as a system (not a checklist)

• Sam strongly supports MEDDIC when used properly:
  • It’s a deal qualification weapon to uncover gaps and next steps
  • Leaders measure it by rep outcomes:
    • if rep isn’t leaving MEDDIC review excited, something is wrong
• Key behavior rules:
  • MEDDIC reviews should feel like gap-hunting (assume missing info)
  • If reviews become “compliance-only,” reps lose:
    • knowledge capture
    • mindshare in the account
    • confidence in the process when deals don’t win

Mandatory truth: “story of the opportunity” > individual checkbox

• Sam rejects: “most important component of MEDDIC?”
• He frames MEDDIC as triangulation:
  • pain → EB → competition → differentiated criteria → how the story connects

Current buying-process complexity (AI governance, committees, addenda)

• Operational challenge in enterprise deals:
  • new steps like AI committees
  • adding AI addenda to MSAs late
• Example:
  • deal delayed due to missing AI addendum, forcing legal review with only ~2 weeks left in a quarter

Their operational response

• Increased triangulation and “ecosystem listening”:
  • consult other (non-competing) software providers to learn what’s changing in that buying process
• Emphasis:
  • assumptions must be tested frequently because buying priorities shift quickly.

Example: priority shift from external event (sales timing risk)

• Example discussed:
  • a large financial institution faced an unexpected $60M data center cost overrun
  • hardware providers covered spend, but no software budget existed at that moment
• Shift occurred in ~10 days, illustrating the need for fast qualification updates and fresh EB intelligence.

Recruiting playbook (coachability + environment design)

• Harness recruiting bias emphasizes coachability and team learning culture.
• Evidence-based hiring questions/methods:
  • Review trajectory “bottom-up” on resume/LinkedIn (predictive of coachability)
  • Ask: “favorite thing about a leader you worked with” (signals whether candidates value education/development)
  • Ask about books/podcasts, feedback recency, handling of feedback
  • Ask: “deal you’re most proud of” and require them to walk through how they qualified it
  • Ask: “deal you lost and what you learned”
  • Require evidence they understand and can apply MEDDIC in real deals (not just “we took training”)

Leadership/organizational tactics

• Radical candor culture: openly talk what’s going well, what’s not
• Deal review follow-through:
  • after a MEDDIC review, leaders ensure reps leave with at least one specific action item owned by the right person (not “all work on the AE alone”)
• Interviewing technique:
  • separate “story vs facts,” interrupt prepared narratives, direct dialogue to find decision evidence
• Talent war value proposition:
  • compensation matters, but Sam stresses differentiators:
    • durable company-building
    • elite GTM team development
    • leadership development / career growth
    • culture (e.g., radical candor, learning, respect)

Concrete actionable recommendations (implied by the talk)

• POV process
  • Run POV only with champion + mindshare coverage across technical governance areas
  • Require SE leader sign-off and CRO sign-off
  • Make POV success measurable and tied to a business-case hypothesis
• EB alignment
  • Get EB alignment before running POV (problem relevance + decision criteria)
• Champion management
  • Reassess champion suitability when deal size increases (upgrade champion if scaling)
  • Build trust via “deposits” before heavy quantification asks
• MEDDIC
  • Run it as gap-and-next-step hunt, not a checklist
  • Use it to generate excitement and a clear road map
• Discovery
  • Quantify pain by extracting the metrics the customer actually uses; ensure pain is real/top-50 relevant
  • If pain can’t be quantified, likely issue is lack of trust with the “champion”
• Buying-process monitoring
  • Stay current with AI-related procurement steps (committees, addenda)
  • Use triangulation with other software providers to learn what’s changing earlier than competitors

Key metrics / KPIs explicitly mentioned

• Growth metric:
  • ARR: < $1M → $100M in 5 years
• Operational time metric:
  • ~40% recruiting
  • ~20% customer-facing selling
• POV mix:
  • ~30–40% workshop-style POVs
  • ~60% install-in-customer-environment POVs
• Technical/platform scale:
  • platform consists of ~14 products
• Timing/deal disruption examples:
  • missing AI addendum creates delay risk, especially with only ~2 weeks left in quarter
  • external disruption example: customer had $60M data center cost overrun (budget shift impacting software projects)

Presenters / sources

• Sam Costello — Chief Revenue Officer, Harness
• John McMahon — Host, Revenue Builders Podcast; Force Management co-founder (as referenced in intro)
• John Kaplan — Co-host / Force Management co-founder (as referenced in intro)