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 is fueling 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 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 has delivered software used by over 140,000 field professionals, impacting millions of users and contributing to $10B+ in built projects. Many of us come from the field ourselves, giving us a deep understanding of the industry’s unique challenges.

After years of building the “brain” of construction, we’re now launching production-ready AI agents, starting with intelligent document processing and Q&A, and rapidly expanding into core operational workflows. Our team has doubled in the past year, and with 65+ employees (25+ engineers), we’re scaling fast and entering a period of hypergrowth. This is a rare opportunity to join at an inflection point.

About the role

We’re hiring a Revenue Enablement Lead to reduce new seller ramp time, increase seller efficiency, and improve execution consistency across mid-market and enterprise motions, including complex, multi-stakeholder deals. This is a hands-on builder role for someone who thrives in fast-paced environments, is deeply data-driven, and uses AI to deliver fast time-to-value enablement.

A key part of this role is enabling enterprise-grade execution: stakeholder strategy, multi-threading, decision process/criteria clarity, mutual action plans, and security/procurement readiness.

While this is a revenue enablement role, Sales enablement across mid-market and enterprise motions (BDR/AE/SE) will be the primary focus for 2026. The scope also includes CS and Implementation enablement as needed, especially where it supports lifecycle continuity (handoffs, expectation-setting, renewal/expansion readiness).

This is a hybrid role where Enablement and Sales Operations are both core responsibilities. As part of a lean three-person Revenue Operations team, you'll need versatility to backfill across functions. You'll partner with RevOps and Revenue Leadership to operationalize processes, reinforce standards through coaching and training, and create lightweight inspection rhythms that improve outcomes without adding bureaucracy.

The realities (read this before applying)

This is a hyper-growth environment:

• 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 - and 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 to build off pre-existing infrastructure, this role will be frustrating. If you like building, iterating, and shipping fast, you’ll thrive.

What you’ll be responsible for

1) 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).

2) 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.

3) Qualification & execution operating system

• Use MEDDPICCR as the qualification and deal inspection framework—especially for complex, multi-stakeholder opportunities.

• Embed 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

• Keep it pragmatic: frameworks should increase speed and clarity—not create paperwork.

4) 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.

5) 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).

6) 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 MEDDPICCR 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.

7) Lifecycle continuity support

• Support enablement for Sales→Implementation→CS continuity where it improves outcomes (handoff quality, expectation-setting, value framing, renewal readiness inputs).

8) 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)

Early focus will be:

• Accelerating ramp for new BDRs/AEs/SEs through clearer readiness standards, coaching cadence, and practical certifications

• Shipping a small set of high-usage, stage-based assets that improve seller efficiency fast

• Adapting MEDDPICCR for usage across GTM

• Tightening core sales operations adoption in HubSpot (stages/fields/handoffs/inspection), in partnership with RevOps

• Establishing lightweight measurement for enablement impact (ramp and execution signals)

(Exact priorities may evolve as the business changes.)

What we’re looking for

Must-haves

• Experience enablin