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 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.
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
🏥 4 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.
