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Toronto, Ontario, Canada
Remote only
This position is listed on behalf of a partner company, who manages all applications and next steps. Our partner is looking for a Director, Expansion & Powered Admin Services based in Canada.
This is a senior, hands-on revenue leadership role focused on building an expansion engine within an established customer base.
You will own expansion revenue while developing a repeatable land-and-expand motion across multiple product and service lines.
The role also introduces a new Powered Admin Services channel through technology partnerships with third-party fund administrators.
You’ll combine strategic leadership with direct selling, personally owning deals while building and coaching a high-performing team.
Success will depend on turning customer data, product adoption signals, and whitespace analysis into actionable account strategies.
You’ll work closely with Sales, Customer Success, Fund Administration, Partnerships, Marketing, Product, and Revenue Operations.
This is a high-autonomy build environment suited to a player-coach who enjoys creating structure where the playbook is still being defined.
Own and deliver an expansion ARR quota while remaining directly involved in selling, managing opportunities from prospecting through close.
Build an expansion pipeline from the existing customer base rather than relying solely on centrally routed opportunities.
Assess the installed base to identify whitespace, wallet-share opportunities, adoption gaps, and accounts with structural barriers to expansion.
Develop prioritized account plans and establish qualification standards and repeatable sales plays for different products and customer segments.
Create systematic lead flows from Customer Success and Fund Administration signals, including product usage, fund launches, and relevant customer lifecycle events.
Develop an adoption-first expansion strategy that uses product engagement, education, and training to create opportunities for paid expansion.
Assess the Powered Admin Services market, identify target administrators and buyers, and lead initial partner conversations and deals.
Work with Product and Fund Administration leadership to define Powered Admin Services packaging, commercial boundaries, and white-label capabilities.
Evaluate the potential for a dedicated Powered Admin Services sales function and establish the data-driven case for additional investment.
Partner with existing sales talent to establish the expansion motion, then hire, onboard, and develop additional sellers as the business scales.
Own ramp plans, pipeline reviews, deal coaching, and MEDDPICC-based sales execution while determining appropriate territory and book-of-business structures.
Establish clear account-ownership rules and handoff processes between account executives and expansion sellers.
Build an operating cadence across Customer Success, Fund Administration, Sales, Marketing, Partnerships, and Revenue Operations.
Provide Marketing with customer segments and behavioral signals that can support targeted expansion campaigns.
Own reporting for expansion pipeline, ARR, product attach rates, time-to-first-expansion, and adoption-to-paid conversion.
Regularly assess and refine routing rules, engagement models, and the broader expansion and Powered Admin Services strategy.
Use AI and internal tooling to automate whitespace scoring, account planning, signal detection, and other revenue workflows, focusing on redesigning work rather than simply adding software.
8+ years of experience in SaaS or fintech revenue roles, including meaningful experience with expansion, installed-base selling, or land-and-expand motions.
Proven history of carrying and achieving a revenue quota, whether through Sales, Customer Success, or another customer-facing revenue function.
Experience building an installed-base or land-and-expand motion, including adoption-led selling, usage-based signals, lead scoring, and cross-functional opportunity generation.
Demonstrated people leadership experience, ideally including building and developing a team from an early stage while remaining personally involved in customer deals.
A strong player-coach mindset, with a willingness to balance strategic planning with hands-on execution.
Comfort operating in ambiguous, evolving environments where processes, policies, and commercial motions are still being established.
Strong Salesforce expertise and the ability to define business and data requirements for Revenue Operations and related tooling.
Demonstrated use of AI to create measurable efficiency in revenue organizations, particularly through workflow redesign and automation.
Strong cross-functional communication and collaboration skills, with the ability to influence Sales, Customer Success, Product, Marketing, Operations, and services teams.
Experience selling technology to fund administrators or working within a business serving fund administrators is highly valued.
Private markets experience or experience selling financial technology to institutional buyers is a strong advantage.
Experience working alongside a professional services organization, including understanding how delivery capacity, margins, and operational constraints influence commercial decisions.
Experience developing white-label, OEM, powered-by, or similar technology partnership models is an advantage.
Competitive compensation package including base salary, commission, and equity.
U.S. base salary range for the role of $160,000–$200,000; Canadian compensation is determined based on location, experience, skills, and applicable local requirements.
Health, dental, and vision coverage for employees and eligible family members.
Life insurance.
Mental wellness coverage.
Fertility and growing-family support.
Flexible paid time off in addition to company-paid holidays.
Paid family, medical, and bereavement leave.
Retirement savings plans.
Allowance to customize your home office and technology setup.
Annual professional development stipend.
Remote work environment with flexibility across eligible locations.
