Trunk Tools, Inc. is hiring a Revenue Enablement Lead

Trunk Tools, Inc. is hiring a Revenue Enablement Lead to drive readiness and performance for our rapidly growing sales team. In this role, you will design and execute enablement programs that directly support our mission to transform the construction industry with AI.

What You'll Do

• Build and run onboarding and internal certification programs for BDRs, AEs, and SEs with clear readiness standards.
• Create repeatable coaching loops including call reviews, role plays, skill drills, and deal support.
• Deliver in-the-flow assets like discovery checklists, demo narratives, and objection handling guides to accelerate rep effectiveness.
• Establish SPICED as the shared operating system across GTM teams and MEDDPICCR for complex enterprise deals.
• Embed frameworks into coaching scorecards, deal review prompts, handoff checklists, and CRM reinforcement.
• Enable reps to run complex enterprise deals with repeatable plays for stakeholder mapping, mutual action plans, and negotiation.
• Use AI to accelerate enablement creation, iteration, and delivery from call transcripts and other data.
• Partner with RevOps to operationalize stage definitions, required fields, pipeline inspection rhythms, and handoff standards.
• Support enablement for Sales→Implementation→CS continuity to improve handoff quality and renewal readiness.
• Flex into adjacent needs like enablement ops, rollout/change management, documentation, and special projects.

What We're Looking For

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

Nice to Have

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

Technical Stack

• HubSpot
• Apollo
• Gong
• Zapier
• Planhat

Team & Environment

You will join a lean team in a hyper-growth environment with 65+ employees (25+ engineers). Our culture is close-knit and collaborative, where every voice is heard as we work to build a more productive and safer construction industry.

Benefits & Compensation

• Competitive salary and stock option equity packages
• 3 Medical Plans to choose from including a 100% covered option
• Dental and Vision Insurance
• Learning & Growth stipend
• Flexible long-term work options (remote and hybrid)
• Free lunch provided in the office in NYC & Austin
• Unlimited PTO
• IRL / In-Person retreats throughout the year

Work Mode

This role operates on a hybrid basis and is open to candidates located in NYC or Austin.

Trunk Tools, Inc. is an equal-opportunity employer, committed to building an inclusive environment where you can be you. We 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.