Director of Sales Strategy and Enablement

We’re looking for someone with strong sales instincts, analytical depth, and a builder mindset to help us grow revenue and improve how we sell.

You’ll work directly with our CEO and Co-Founder and partner with Sales, Marketing, and Operations to identify opportunities, develop solutions, and put them into practice. Your work will span sales funnel optimization, customer and competitive insights, pricing and packaging, and building AI-powered tools that make our sales team more effective.

You’ll personally analyze data, listen to customer conversations, build workflows and tools, and run experiments. Success means delivering measurable improvements in conversion, revenue per consultation, and sales productivity.

• Analyze the full customer journey—from lead acquisition and consultation booking through enrollment—to identify where we lose opportunities and how to improve.
• Turn funnel data, sales conversations, and lost-deal patterns into specific actions around qualification, recommendations, follow-up, and closing.
• Build reporting that helps the team understand conversion, average package value, sales cycle, acquisition efficiency, and performance by channel, program, and salesperson.
• Partner with sales leadership to implement improvements and measure their impact.

• Regularly review prospect calls and work directly with Enrollment Managers to understand customer needs, objections, and buying decisions.
• Study market offerings, pricing, positioning, sales experiences, and proof of outcomes.
• Translate those insights into recommendations for new programs, bundles, package features, and positioning.
• Partner with delivery teams to assess feasibility and economics, launch pilots, and determine what should scale.

• Personally prototype and build tools that help our sales team prepare for calls, recommend programs, create proposals, follow up, and access relevant information.
• Use AI-assisted coding, low-code tools, and workflow automation to move quickly from an idea to a working solution.
• Connect tools with our CRM and existing systems, with appropriate attention to data quality, permissions, and reliability.
• Own rollout, documentation, adoption, and ongoing improvement; measure whether tools save time and improve results.

• Own improvements to CRM workflows, lead routing, pipeline stages, follow-up automation, and sales-to-Student-Success handoffs.
• Maintain clear definitions and reliable data so teams can make decisions from a consistent view of performance.
• Identify manual work and operational bottlenecks, then implement practical solutions.
• Prioritize projects based on expected commercial impact and effort, and carry them through to completion.

• Approximately 5–8 years of relevant experience across Revenue Operations, Sales Operations, GTM Strategy, Growth, or commercial business operations.
• Relevant experience managing and growing a team
• Strong sales judgment developed through direct selling or close, sustained work with a sales team. You understand discovery, objections, buying motivations, and how deals progress.
• A record of personally delivering improvements in conversion, deal value, sales productivity, or revenue growth.
• Hands-on experience configuring a CRM, building workflows, and using data to diagnose business problems.
• Practical experience building AI tools or automations that other people actually use. You can show us what you built and explain your contribution.
• Strong analytical skills, including comfort with spreadsheets, funnel analysis, dashboards, and experiment measurement.
• The ability to move from an ambiguous problem to a working solution with limited direction.
• Clear communication and the ability to earn trust with salespeople, technical partners, and senior leaders.

• Consultative B2C sales, education, marketplaces, or high-consideration services.
• Pricing, packaging, competitive research, or launching new offers.
• HubSpot or a comparable CRM; automation platforms such as n8n, Make, or Zapier; and AI-assisted development tools.
• SQL, APIs, or scripting skills that help you independently build and troubleshoot solutions.
• Bonus: Prior experience as an Account Executive, sales consultant, founder, or early commercial hire.

In your first 30 days: Develop a clear understanding of our sales process, customer conversations, funnel performance, and systems. Identify the highest-value opportunities and ship an initial improvement.

Within 60 days: Launch useful sales tools and automations along with measurable commercial experiments, with clear ownership, adoption, and success criteria.

Within 90 days: Show evidence of impact, establish a prioritized roadmap, and create a repeatable process to turn insights into improvements.

You’ll work directly with the co-founder, have access to real customer feedback, and own projects from initial insight through implementation. You’ll have room to shape how we sell, what we offer, and how we use AI across the revenue organization.

• Amazing people with a great vision and values
• Mission-driven team culture focused on student success
• Your work directly impacts the lives and careers of students across the globe
• Health, dental, and vision insurance, base plans 100% employer paid
• Pre-tax benefits (FSA, DCFSA, HSA, Commuter)
• Flexible paid time off (PTO) and paid holidays
• 401(k) with company match

The targeted OTE for this role is: $180K-$220K OTE. Actual compensation is dependent upon several factors, including the applicant's experience, knowledge, skills, and abilities, as well as internal equity among our team and geographic location. The pay ratio between base pay and target incentive will be finalized at the offer. The pay range is subject to the discretion of the Company.