Director, Services

Jasper • ,

5d • $184,000 - $230,000 • Remote

About The Position

As a Director of Services at Jasper, you will own the strategy, operating model, and growth of our Services organization at a pivotal moment – as Jasper evolves from a product-led to a services-led motion. You will lead three service pillars – implementation, enablement, and advisory – and shape how Jasper turns cutting-edge AI into measurable, compounding value for our customers. This is a builder's role: you will up-level implementation into consultative onboarding, stand up enablement on real learning-methodology frameworks, grow our advisory practice, and put in place the commercial and operational backbone that lets Jasper answer, for the first time, what was sold, how long delivery took, and what the true margin was on every engagement.
You will operate as a hands-on player-coach – equally at home in a customer pitch, a senior leadership conversation, and in-the-weeds work with your team, often in the same day – while developing a talented team and evangelizing the strategic role of Services across the company.
This fully remote role reports to the VP, Customer Success and is open to candidates located anywhere in the continental US.

Requirements

• 10+ years in professional services, customer success, implementation, or solutions-delivery leadership at a SaaS, AI, or enterprise software company, including experience leading managers as well as senior individual contributors.
• AI fluency – a working understanding of core AI concepts (LLMs, agents, copilots, tokens, credits, context windows, RAG, and data governance) applied in the context of customer services: guiding customers through AI adoption and maturity and translating the platform into real workflow outcomes.
• A commercialization mindset – a proven ability to evaluate whether service offerings are fit for purpose, define pricing and packaging, and grow Services into a strategic, revenue-relevant motion.
• Player-coach leadership – you lead from the front, staying hands-on with process and customers rather than operating solely at a distance.
• Strong customer-facing and cross-functional instincts – you are the person others pull into the room to inspire confidence, and you can influence Sales, Product, and Customer Success without direct authority.
• Experience leading a team through a restructure or reorg, with a demonstrated ability to re-rally people around a new vision and lead with empathy.
• The ability to "code-switch" fluidly across contexts in a single day – customer pitches, senior leadership conversations, and in-the-weeds teamwork.

Nice To Haves

• a background in formal learning methodology or curriculum design (learning objectives, outcomes, structured program design), ideally applied to customer enablement.
• experience standing up or scaling professional-services automation and resource/capacity-planning infrastructure.
• exposure to AI-transformation services within EdTech or B2B SaaS environments.

Responsibilities

• Define and own the vision, strategy, and operating model for Jasper's Services organization across three pillars – implementation, enablement, and advisory – aligned to our shift toward a services-led motion.
• Lead, coach, and develop a multidisciplinary team spanning the three pillars, operating as a hands-on player-coach rather than a purely directive manager.
• Up-level implementation from task execution into consultative, outcomes-driven onboarding that compresses time-to-value for customers.
• Build out enablement into productized-yet-bespoke customer training grounded in formal learning methodology – clear objectives, measurable outcomes, and structured curriculum design.
• Grow the advisory practice, helping customers navigate AI adoption and maturity, and expand its scope and impact over time.
• Define the commercial model for Services – assess whether offerings are fit for purpose, shape pricing and packaging, and evangelize Services internally across Sales, Customer Success, and leadership.
• Partner cross-functionally and engage directly in customer-facing conversations, including pre-sales and deal moments, to inspire confidence and win customer trust.
• Own the operational backbone for Services delivery – resource capacity planning and professional-services automation (time tracking across pre-sales, billable, non-billable, PTO, and internal productive time) – including a dotted-line responsibility for the infrastructure serving the Forward-Deployed Engineering (FDE) team, so Jasper can measure delivery effort and true engagement margin.

Benefits

• Comprehensive Health, Dental, and Vision coverage beginning on the first day for employees and their families
• 401(k) program with up to 2% company matching
• Equity grant participation
• Flexible PTO with a FlexExperience budget ($900 annually) to help you make the most of your time away from work
• FlexWellness program ($1,800 annually) to help support your personal health goals
• Generous budget for home office setup
• $1,500 annual learning and development stipend
• 16 weeks of paid parental leave

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed