Director – Client Strategy, Small and Medium Businesses

About the role…

As Director of Client Strategy, SMB at ShopMy, you will build and lead a brand-new pod from the ground up - designing and running a one-to-many service model that delivers retention and platform adoption at scale. Your team will support 150-200+ brands each through scaled programs: webinars, lifecycle and CRM campaigns, customer education, and self-serve resources.

This is a builder's role. Success looks less like classic account management and more like systems design - driving best-in-class retention, product adoption, and client experience through scaled and digital resources.

Your role is critical in driving retention, growth, and platform adoption - while actively developing your team, shaping cross-departmental initiatives, and helping define the future of ShopMy through thoughtful leadership and product feedback.

What You’ll Do:

• Build the pod from zero to one - define the service model, ways of working, KPIs, and team structure for a segment we've never served this way before
• Design the one-to-many motion - webinar programs, CRM and lifecycle campaigns, in-product education, and scaled onboarding that drive adoption and retention without one-to-one touchpoints, partnering with Product, Marketing, and Support to deliver exceptional client outcomes
• Stand up customer education - learning paths, LMS, self-serve content, and the operating cadence behind them
• Drive retention and upgrade performance, including a measurable path from entry-level packages into product adoption, spend, and package upgrades
• Actively coach and develop your team - providing frequent feedback, engineering growth opportunities, owning onboarding, and cultivating top-tier talent
• Be a visible voice for the segment, hosting or producing webinars and scaled client-facing programming
• Partner with Product to translate SMB needs into roadmap priorities — this segment requires self-serve solutions, not headcount
• Embed AI-driven workflows that expand what a small team can deliver, and help shape how AI is deployed across Client Strategy
• Align SMB strategy with company priorities, partnering with peers and leadership to drive buy-in cross-functionally

You Are Energized By:

• Building something from scratch - writing the playbook rather than inheriting one
• Designing systems and processes that work at scale, and getting energy from the leverage they create
• Solving for retention across a large, diverse book without one-to-one relationships
• Turning ambiguity into structure, and structure into repeatable programs
• Partnering with Product and Marketing as closely as with clients
• Leading and developing a team in a fast-paced, remote startup environment
• The creator economy and the brands building in it

What We Are Looking For:

• 8-10+ years of experience in customer success, account management, or customer operations, with meaningful time spent in the SMB segment
• Direct experience standing up a one-to-many, scaled, or digital service model - you've done this transition before, not just observed it
• Proven ownership of scaled retention programs: webinars, CRM/lifecycle campaigns, customer education, or LMS build-outs
• Background as an account manager or CSM earlier in your career - you know what the one-to-one motion delivers before you replace it
• Strong leadership skills and proven experience managing and mentoring a team
• Systems thinking and operational rigor - you're comfortable owning tooling, process design, and measurement
• Ability to partner with Product to shape self-serve and automated solutions
• Bachelor's degree required

Bonus Points:

• Deep passion and understanding of the creator economy
• Prior experience in SaaS Customer Success at a company that scaled its service model as it grew
• Experience in a remote startup environment
• NYC-based is a plus, but not required

New York Pay Range 150000 - 175000 USD