Director, Professional Services & Technical Success

Thinkific is a learning commerce platform that helps learning businesses turn knowledge into impact. By bringing together community, courses, and content with commerce, we power transformative learning experiences that help businesses grow their revenue—and reach millions of learners around the world.

We’re a team of 300+ Thinkers building products that matter. Every role at Thinkific contributes to raising the bar for online learning, supporting learning businesses, and creating real-world impact. You’ll work alongside curious, collaborative teammates who care deeply about what they build and who they build it for.

We’re committed to a fair, inclusive, and human hiring experience. Our team is here to guide you every step of the way, so you always know what to expect!

Are you excited by the opportunity to shape how customers experience Thinkific from pre-sale to launch and beyond? We're looking for a Director, Professional Services & Technical Success  to join us at Thinkific.

As the Director, Professional Services & Technical Success, you will define, build, and scale a Professional Services practice, designing our service offerings, driving services revenue, and delivering measurable value for our most complex customers. In this role, you will own the strategy and execution for three critical functions: Professional Services, Sales Engineering, and Launch, to ensure our customers' technical success and realization of the full power of the Thinkific platform.

This is both a strategic and highly operational role. In its current phase, approximately 70% of your time will be spent directly leading and scaling three critical functions: Professional Services, Sales Engineering, and Launch, while roughly 30% will focus on designing, building, and documenting the systems that power the program.

Your goal will be to drive retention and adoption while leading a high-performing technical services organization. Here's how you'll accomplish this:

Pre-Sales, Launch, and Professional Services Excellence

You will directly own and ensure technical success from the first demo to a successful launch and beyond for high value prospects and the most complex customers. This includes:

• Lead and scale a high-performing organization encompassing Professional Services, Sales Engineering, and Implementation Specialists (Launch), with direct accountability for team leaders. This is a manager of managers role, and includes responsibility for the mentorship, performance, and professional development of those leaders

• Build and lead the Professional Services Practice: Define, develop, and iterate on Thinkific's Professional Services offerings, including service tiers, scoping methodology, delivery frameworks, and repeatable playbooks. Own pricing and packaging of Professional Services offerings in collaboration with RevOps and Sales, ensuring services are commercially viable and competitively positioned

• Drive Professional Services revenue growth by increasing attach rate, expanding service scope, and identifying upsell opportunities within the customer base

• Deliver high value consulting, custom migrations, and complex technical integrations for our most demanding customers

• Develop utilization targets, margin models, and operational metrics that make the Professional Services practice accountable and scalable

• Collaborate Cross Functionally: Act as the voice of technical services within the organization. Work with Product and Engineering to provide feedback on customer needs, and with Sales to ensure our technical capabilities align with our go-to-market strategy

Operationalize for Scale

In addition to managing and growing a high-performing technical services team, you will design and operate a high leverage, scaled operational framework to ensure the department is operating effectively and driving feature adoption across the broader technical services department. Specifically, you will:

• Champion the use of AI tools and automation across the Technical Services organization, identifying where AI can accelerate delivery, reduce manual effort, and improve the customer experience at scale

• Establish a data driven framework in partnership with Customer Success and Sales leadership for identifying time to value challenges and poor feature adoption, growth opportunities, and segment specific intervention triggers across the customer base and Thinkific platform adoption

• Define and operationalize clear signal thresholds in partnership with Product and Engineering to address new feature adoption rates, technical roadblocks or integration challenges, and post launch customer engagement that determine engagement pathways

• Lead high profile projects and drive key feature adoption initiatives, including hiring, complementing your primary program development responsibilities for the technical services team

What We're Looking For

Required

• Has 10+ years of experience in technical customer facing roles (Professional Services, Consulting, or Technical Account Management), with at least 5 years in a leadership position at a SaaS company

• Has demonstrated experience building and leading a Professional Services organization. You have designed service offerings, built delivery frameworks, and grown a Professional Services practice, not just managed within one

• Has manager of managers experience. You have led teams through team leads or managers, and have a track record of developing leaders, not just individual contributors

• Is a proven leader with experience managing multidisciplinary teams and a track record of hiring, coaching, and retaining top technical talent

• Has technical depth and understands the SaaS model inside and out. You are comfortable discussing APIs, SSO, webhooks, and complex integrations, and can translate this tech speak into plain language for any audience

• Has strong commercial acumen and understands how Professional Services drives revenue, with experience in pricing, packaging, and margin management

• Has demonstrated ability to leverage AI tools in a professional context, whether to accelerate service delivery, enhance team productivity, or improve customer outcomes

• Is a strategic thinker who looks beyond day to day execution and designs scalable processes that work just as effectively for 1,000 customers as they do for 10

• Is a strong communicator: a compelling storyteller who can speak to executive stakeholders and technical individual contributors with equal confidence

• Loves to learn and grow. They've found (and keep looking for) ways to level up their skills in this field, whether that's through formal education, gaining professional experience, or maybe even building their own business

Nice to Have

• Experience in the e-learning or LMS space

• Familiarity with tools like Salesforce, Zendesk, and Jira

We’re committed to fair and transparent pay that reflects both where you are and where you can grow to. This role has a salary range of $150,000 - $210,000 CAD in Canada, designed to capture the full journey from developing skills to excelling in the position. Most new hires start between the minimum and midpoint, which aligns with being fully capable in the role. Salaries above the midpoint are typically reserved for team members who have demonstrated strong, consistent performance, deep expertise, and a significant positive impact within the role.

For high-demand or hard-to-fill positions like this one, we may hire above the midpoint for candidates who bring exceptional experience, skills, or impact potential.

Diversity, Equity, Inclusion and Belonging & Accessibility

This is just our initial idea of who we’re looking for! At Thinkific, we know that people have unique career journeys. If your experience is close to what we’ve described but you feel that you might be missing a few of the requirements, please still apply! We believe in equal opportunity and are committed to diversity, equity, inclusion, and belonging across every facet of our business.

We’re also committed to providing a comfortable and accessible interview experience for every candidate. If there are any accommodations our team can make throughout our hiring process (big or small), please let us know.

What you can expect if you join Thinkific:

An amazing team of talented, passionate, and kind Thinkers. Together, we’ve built an amazing, award-winning culture —we’re a Certified Great Place to Work and one of Canada’s Most Admired Corporate Cultures by Waterstone!

The chance to build, improve, and innovate on a platform that’s driving positive impact for thousands of businesses and millions of students around the world.

A competitive compensation package including base salary, equity, team-wide bonuses, and an Employee Share Purchase Plan.

Flexible Paid Time Off to maintain mental and physical health. Our team is encouraged to take a minimum 4 weeks of vacation, plus Thinker Holidays (extended long weekends in the summer) and time off for the December holiday season.

Health Benefits and Wellness: Comprehensive benefits starting on Day 1 include health, vision, and dental coverage for you and your family, $3,000 for mental health care, a short-term health plan, and an additional $900/year health or personal spending account. Plus, family friendly benefits include generous parental leave top-ups for up to 32 weeks, as well as fertility coverage and personalized return to work options.

3 Paid Volunteer Days each year to give back to your community and support the causes you care about.

Flexible Work . Choose to work from home from anywhere in Canada, at our Vancouver HQ, a co-working space, or anywhere there’s wifi for a change of scenery.

⬆️ Learning & Growth. An annual $2,000 CAD Learn and Grow fund for conferences, seminars, or courses, plus training, mentorship, coaching, and internal promotion opportunities.

A home office setup so you’re ready to succeed with a company-owned Macbook Pro and a budget to order a desk, chair, or any accessories to help you work comfortably and productively.

A place where you can bring your whole self to work . We know that different perspectives lead to amazing ideas, more innovation, and, ultimately, our success as a company. We welcome applicants of all backgrounds, experiences, beliefs, identities, and statuses. Whoever you are—we can’t wait to meet you!

The Thinkific Vancouver office operates on the traditional, ancestral, and unceded territories of the xʷməθkʷəy̓əm (Musqueam), Sḵwx̱wú7mesh (Squamish), and Sel̓íl̓witulh (Tsleil-Waututh) Nations of the Coast Salish People. We encourage everyone to learn more about the original caretakers of the land that you currently occupy.