At Trunk Tools, weâre 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, weâre 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 industryâs unique challenges.
After years of building the âbrainâ of construction, weâre 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), weâre scaling fast and entering a period of hypergrowth. This is a rare opportunity to join at an inflection point.
Weâre 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.
This is a hyper-growth environment:
Priorities shift; youâll need to adapt quickly and make tradeoffs.
Youâll build v1 fast, iterate, and improve continuously.
You wonât have perfect inputs, perfect tooling, or unlimited resources - and youâll still be expected to deliver outcomes.
Youâll 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, youâll thrive.
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 supportâespecially for early-tenure reps.
Define âwhat good looks likeâ for each role at each stage (a practical readiness framework).
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 âtradeâ frameworks.
Reduce reliance on live training by building scalable enablement that reps can actually use day-to-day.
Use MEDDPICCR as the qualification and deal inspection frameworkâespecially for complex, multi-stakeholder opportunities.
Embed MEDDPICCR where appropriate into:
coaching scorecards and call review standards
stage expectations and deal review prompts
handoff checklists (BDRâAE, AEâSE, SalesâCS)
CRM reinforcement (fields/prompts/templates), in partnership with RevOps
Keep it pragmatic: frameworks should increase speed and clarityânot create paperwork.
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 (âtrade, donât discountâ)
Tailor enablement by segment/motion while keeping the system simple.
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 â curate â QA â publish â reinforce.
Operate responsibly with customer/prospect data (approved tools and safeguards).
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 â Implementation â CS)
Translate process changes into training, reinforcement, and measurable adoption - without adding unnecessary friction.
Support enablement for SalesâImplementationâCS continuity where it improves outcomes (handoff quality, expectation-setting, value framing, renewal readiness inputs).
Comfortably flex into adjacent needs when required (enablement ops, rollout/change management, documentation, special projects) while staying anchored to enablement outcomes.
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.)
Experience enablin
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