Director, Services

This is a fully remote position, open to applicants in California.

📋 Description

• Establish and take ownership of the vision, strategy, and operational framework for Jasper's Services organization across three key areas: implementation, enablement, and advisory, in alignment with our transition to a services-led approach.

• Guide, mentor, and nurture a diverse team across the three areas, functioning as a hands-on player-coach instead of just a directive manager.

• Elevate implementation from mere task execution to a consultative, outcomes-focused onboarding process that reduces time-to-value for our customers.

• Develop enablement into a productized yet tailored customer training program based on formal learning methodologies, including clear objectives, measurable outcomes, and structured curriculum design.

• Expand the advisory practice, assisting customers in navigating AI adoption and maturity while increasing its scope and impact over time.

• Establish the commercial framework for Services by evaluating the suitability of offerings, shaping pricing and packaging, and advocating for Services within Sales, Customer Success, and leadership.

• Collaborate cross-functionally and engage directly in customer-facing discussions, including pre-sales and deal moments, to instill confidence and earn customer trust.

• Manage the operational foundation for Services delivery, including resource capacity planning and professional services automation (time tracking across pre-sales, billable, non-billable, PTO, and internal productive time), along with a dotted-line responsibility for the infrastructure supporting the Forward-Deployed Engineering (FDE) team, allowing Jasper to measure delivery efforts and true engagement margins.

⛳️ Requirements

• Over 10 years of experience in professional services, customer success, implementation, or solutions-delivery leadership at a SaaS, AI, or enterprise software company, with experience in leading both managers and senior individual contributors.

• Proficiency in AI – a solid understanding of fundamental AI concepts (LLMs, agents, copilots, tokens, credits, context windows, RAG, and data governance) as applied to customer services: assisting customers through AI adoption and maturity while translating the platform into tangible workflow results.

• A commercialization focus – a demonstrated capability to assess the suitability of service offerings, define pricing and packaging, and evolve Services into a strategic, revenue-generating initiative.

• Player-coach leadership style – you lead proactively, remaining engaged with processes and customers rather than functioning solely from a distance.

• Strong instincts for customer interaction and cross-functional collaboration – you are the person colleagues approach for inspiration and can sway Sales, Product, and Customer Success despite lacking direct authority.

• Experience in guiding a team through a restructuring or reorganization, with a proven ability to re-engage people around a new vision while leading with empathy.

• The ability to fluidly adapt communication styles across various contexts in a single day, including customer pitches, senior leadership discussions, and detailed teamwork.

• Nice to have: experience in formal learning methodologies or curriculum design (learning objectives, outcomes, structured program design), preferably applied to customer enablement.

• Nice to have: experience in establishing or scaling professional services automation and resource/capacity-planning frameworks.

• Nice to have: familiarity with AI-transformation services in EdTech or B2B SaaS settings.

🏝️ Benefits

• Comprehensive Health, Dental, and Vision coverage starting on the first day for employees and their families.

• 401(k) program with up to 2% company matching.

• Participation in equity grants.

• Flexible PTO along with a FlexExperience budget ($900 annually) to enhance your time away from work.

• FlexWellness program ($1,800 annually) to support your personal health objectives.

• Generous budget for home office setup.

• $1,500 annual stipend for learning and development.

• 16 weeks of paid parental leave.