Revenue Enablement Lead

At Trunk Tools, we’re the leading AI company revolutionizing construction—the second‑largest industry on earth. We recently raised a $40M Series B led by Insight Partners, bringing our total funding to $70M from top‑tier investors including Redpoint and Innovation Endeavors. This new round fuels our next phase of growth as we scale AI agents across the jobsite. Our mission is to build the future of construction through intelligent automation. Despite being a $13 trillion‑plus industry, construction still runs largely on analog processes—we’re changing that by embedding AI directly into field operations. Founded by builders and technologists (Stanford, MIT), our team delivers software used by over 140,000 field professionals, impacting millions of users and contributing to $10 B+ in built projects.

Base pay range

$110,000.00/yr – $143,000.00/yr

The realities (read this before applying)

• Priorities shift; you’ll need to adapt quickly and make tradeoffs.
• You’ll build v1 fast, iterate, and improve continuously.
• You won’t have perfect inputs, perfect tooling, or unlimited resources—yet you’ll still be expected to deliver outcomes.
• You’ll own work outside of the job description to keep the business moving.

If you want a narrow scope and want to build off pre‑existing infrastructure, this role will be frustrating. If you like building, iterating, and shipping fast, you’ll thrive.

Ramp & readiness systems

• Build and run onboarding and internal certification programs for BDRs, AEs, and SEs with clear readiness standards.
• Create repeatable coaching loops: call reviews, role plays, skill drills, and deal support—especially for early‑tenure reps.
• Define “what good looks like” for each role at each stage (a practical readiness framework).

Seller efficiency and time‑to‑value enablement

• Deliver in‑the‑flow assets that make reps effective faster: discovery checklists, demo narratives, stakeholder meeting agendas, objection‑handling guides, mutual plan templates, proposal/value summaries, and negotiation “trade” frameworks.
• Reduce reliance on live training by building scalable enablement that reps can actually use day‑to‑day.

Qualification & execution operating system

• Establish SPICED as the shared operating system across GTM teams: common language, consistent deal narratives, and customer‑centric execution.
• Define how SPICED is used day‑to‑day: discovery expectations, deal reviews, handoffs, and “what must be true” by stage.
• Use MEDDPICCR as a complementary enterprise‑grade qualification and deal inspection framework—especially for complex, multi‑stakeholder opportunities.
• Embed SPICED (and MEDDPICCR where appropriate) into:
  • Coaching scorecards and call review standards
  • Stage expectations and deal review prompts
  • Handoff checklists (BDR→AE, AE→SE, Sales→CS)
  • CRM reinforcement (fields/prompts/templates), in partnership with RevOps

Enterprise‑ready selling enablement

• Enable reps to run complex enterprise deals with repeatable plays:
  • Stakeholder mapping + multi‑threading standards
  • Decision process + decision criteria discovery
  • Mutual action plans tied to critical events
  • Security/procurement readiness support (templates, FAQs, talk tracks)
  • Negotiation discipline (“trade, don’t discount”)
• Tailor enablement by segment/motion while keeping the system simple.

AI‑forward enablement engine

• Use AI to accelerate enablement creation, iteration, and delivery (e.g., turning top call transcripts into draft playbooks, talk tracks, onboarding modules).
• Build a repeatable workflow: synthesize → curate → QA → publish → reinforce.
• Operate responsibly with customer/prospect data (approved tools and safeguards).

Revenue Operations support

You will directly contribute to making our GTM process real in the CRM and in weekly execution:

• Partner with RevOps to operationalize and drive adoption of:
  • Stage definitions and exit criteria
  • Required fields/standards that support SPICED consistency and forecasting hygiene
  • Pipeline/deal inspection rhythms (clean, lightweight, consistent)
  • Handoff standards and operational follow‑through (Sales → Implementation → CS)
• Translate process changes into training, reinforcement, and measurable adoption—without adding unnecessary friction.
• Support enablement for Sales→Implementation→CS continuity where it improves outcomes (handoff quality, expectation‑setting, value framing, renewal readiness inputs).
• High‑ownership operating model in a lean team.
• Comfortably flex into adjacent needs when required (enablement ops, rollout/change management, documentation, special projects) while staying anchored to enablement outcomes.

Early priorities (first ~90 days)

• Accelerate ramp for new BDRs/AEs/SEs through clearer readiness standards, coaching cadence, and practical certifications.
• Ship a small set of high‑usage, stage‑based assets that improve seller efficiency fast.
• Standardize SPICED usage across GTM (and align MEDDPICCR for complex enterprise deals).
• Tighten core sales operations adoption in HubSpot (stages/fields/handoffs/inspection), in partnership with RevOps.
• Establish lightweight measurement for enablement impact (ramp and execution signals).

What We’re Looking For

Must-haves

• Experience enabling enterprise/complex sales cycles (multi‑stakeholder deals, mutual action plans, decision process/criteria, and security/procurement workflows).
• Proven ability to improve time‑to‑productivity through onboarding, certifications, coaching, and behavior change.
• Strong data fluency (can diagnose performance gaps, prioritize, and measure impact).
• AI‑forward operator (uses AI to accelerate output with strong QA discipline).
• Comfortable owning enablement and partnering deeply on Revenue Operations (process adoption, CRM reinforcement, inspection rhythms).

Nice‑to‑haves

• Experience with Winning by Design frameworks and implementation in‑the‑flow (especially SPICED).
• Experience enabling Sales Engineers, Implementation/Professional Services, and Customer Success teams.
• Construction tech or similarly complex, multi‑stakeholder enterprise environments.
• Familiarity with Gong and HubSpot enablement/ops workflows.

Tools and Systems

• HubSpot
• Apollo
• Gong
• Zapier
• Planhat

What we offer

• A close‑knit and collaborative early‑stage startup environment where every voice is heard and every opinion matters.
• Competitive salary and stock option equity packages.
• 3 Medical Plans to choose from including 100% covered option, plus Dental and Vision Insurance.
• Learning & Growth stipend.
• Flexible long‑term work options (remote and hybrid).
• Free lunch provided in the office in NYC & Austin – you’ll never go hungry with us!
• Unlimited PTO; we truly believe in work‑life balance and that hard work should be balanced with time for rest and rejuvenation.
• IRL / In‑Person retreats throughout the year.

Please note: All official communication from Trunk Tools will come from an email address ending in @trunk.tools. If you receive outreach from any other domain, please disregard it or report it to us.

At Trunk Tools, we’re working hard to build a more productive and safer environment within the construction industry, and we strive to live by these same values here at Trunk Tools HQ. As an equal‑opportunity employer, we are committed to building an inclusive environment where you can be you. We work hard to evaluate all employees and job applicants consistently, without regard to race, color, religion, gender, national origin, age, disability, pregnancy, gender expression or identity, sexual orientation, or any other legally protected class.

Employment type: Full‑time

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Tagged as: Change Management, Deal Desk, Forecasting, HubSpot, Zapier