Director, GTM Enablement & Training

The Role

We are hiring our first dedicated Sales Enablement & Training Manager. This is not a content-management or LMS-administration role; it is fundamentally a sales training and domain-teaching position. The core mission has two parts: developing talented enterprise AEs who arrive without construction experience into sellers who can hold credible conversations with the people who run construction projects - from project executives to field superintendents - and building the systems that produce those sellers consistently as the organization scales.

Success in this role depends on two capabilities. First, the ability to learn a complex, unfamiliar industry quickly and thoroughly - and to develop genuine expertise in it. Second, the ability to teach it: translating dense field reality into training that turns a generalist seller into someone customers trust.

You will use our AI tools, including our internal Claude instance, to accelerate your own ramp into the construction domain, then teach AEs to learn the same way. You will also build out the supporting enablement function (onboarding, playbooks, certification, and tooling) as the team grows.

Your Day to Day

Build the Enablement Function

• As our founding enablement hire, design and operationalize the company's first formal sales enablement program, establishing its strategy, priorities, and infrastructure.
• Create scalable onboarding programs across GTM roles: AEs first, then SDRs, Solutions Engineers, and Customer Success.
• Develop certification frameworks and role-based competency models.
• Build repeatable, AI-supported training systems that scale with company growth, including self-service delivery and the supporting tooling and LMS stack, so quality instruction doesn't depend on a live session for every rep.

Training & Curriculum Development

• Build your own deep construction expertise first: the project lifecycle, the stakeholders who run jobsites, and the metrics that govern their work. Use AI, including our Claude instance, to accelerate your ramp, then teach AEs to learn the same way.
• Develop curricula that turn generalist AEs into construction experts: persona guides, per-persona discovery questions, and objection libraries grounded in field reality.
• Give reps repeated, realistic practice, including AI role-play against construction personas, and gate certification on demonstrated domain fluency rather than product recall.
• Deliver live and asynchronous training, and coach in the flow of work (call and demo reviews, deal debriefs, role-plays).
• Use AI to accelerate content production from product releases, recorded calls, and SME interviews.

Sales Process & Playbooks

• Build and maintain playbooks across the customer lifecycle: discovery frameworks, qualification, account planning, and deal inspection.
• Develop messaging and talk tracks aligned to our ICPs and buyer personas.
• Embed an enterprise methodology (MEDDICC, Challenger, or consultative selling) and reinforce it so adoption holds.
• Partner with Product Marketing to translate product releases into sales-ready enablement content

Cross-Functional Collaboration

• Partner with Sales Leadership, Product Marketing, Product, Customer Success, and RevOps; translate product releases into sales-ready content and surface gaps through pipeline reviews, call data, and field feedback.

Performance & Analytics

• Define enablement KPIs and measure training effectiveness.
• Analyze onboarding ramp time, time-to-domain-credibility, quota attainment, win rates, certification pass rates, discovery quality, and overall sales productivity.
• Use feedback loops and data insights to continuously improve programs.

What Success Looks Like

Within the first 12 months, this person will:

• Onboarding and certification are live, with construction fluency the bar to be deal-ready.
• New AEs reach that bar faster and more consistently.
• Sharper, construction-grounded discovery shows up in pipeline quality and win rates.
• Most training is self-service and AI-supported, scaling without live sessions.
• Methodology and messaging are applied consistently across the team.

What You Bring

• 8+ years across sales, sales training, and/or enablement, ideally including direct enterprise selling or rep coaching.
• Demonstrated excellence as a teacher and coach, with a track record of developing people from beginner to credible. Strong facilitation, presentation, and adult-learning skills. This is the most important qualification.
• Strong learning agility. You have moved from no knowledge of a complex or technical domain to genuine expertise, and can describe how. You approach mastering an unfamiliar industry as an opportunity rather than an obstacle
• Fluency with modern AI tools and the ability to use them to build training: interactive simulations, adaptive self-service learning, and faster content production. You treat AI as core to making enablement scalable, not as an add-on.
• A solid understanding of enterprise B2B SaaS sales (long, multi-stakeholder cycles involving technical and operational buyers) and fluency in at least one methodology (MEDDICC, Challenger, SPIN, or Command of the Message).
• 0→1 experience, with comfort in ambiguity and a history of building training, onboarding, or sales programs from scratch.
• The ability to create content independently (curricula, playbooks, and certification tracks) without relying on pre-existing templates.

Benefits & Company Culture

• Competitive Base Salary + Equity Package
• Remote first culture (for most roles)
• Comprehensive Health Insurance (Medical, Dental, Vision)
• Home Office Stipend
• Monthly allowance for cell phone and internet
• Flexible PTO, generous company holiday policy

Preferred Experience

• Hands-on experience building AI-enabled or self-service training, such as simulation-based practice, AI-assisted content creation, or conversational knowledge tools.
• Direct experience in construction tech, AEC, industrial SaaS, PropTech, or operational technology, which shortens domain ramp time.
• Familiarity with enterprise procurement and operational or field buyer personas.
• Experience enabling technical sales motions that involve Solutions Engineering.
• Certifications in sales coaching, enablement, training, or leadership development.
• Experience implementing LMS or enablement tooling