Head of Sales and Customer Success

PeopleJoy•Philadelphia, PA

3d•$120,000 - $150,000•Hybrid

About The Position

As the Director of Commercial Activation & Revenue Strategy you'll be critical in designing and maintaining the operational system that turns existing customers into growing revenue assets. Working closely with the CEO and Account Manager you’ll be responsible for developing playbooks for activation, renewals and internal expansion. You’ll also maintain and analyze metrics related to our sales funnel and client engagement to continually refine and improve our sales conversions and increase net revenue retention. In this role, you’ll be the CEO’s strategic partner, directly collaborating to turn sales and renewals into repeatable commercial motions. This means studying adoption/usage dynamics, and renewal politics and building playbooks. Your work will be instrumental in building and scaling the company’s revenue engine—and ultimately, the company’s success. What does a Director of Commercial Activation & Revenue Strategy do, anyway? In simple terms, they help generate more revenue from current customers by getting employees to use the benefit and stick with it.

Requirements

Operated in B2C SaaS sales or adjacent categories (benefits, financial wellness, workforce, education, behavioral health, navigation, talent mobility)
Worked in early-stage revenue environments pre-CRO and helped them scale
Scaled usage/activation → renewal → expansion → NRR motions
Experienced founder-led sales and non-linear buyer sequences
Navigated CHRO, Total Rewards, HR Ops, and Finance stakeholder dynamics
Built commercial playbooks before inheriting them

Responsibilities

Set the big goals: Own NRR targets and map the steps needed to hit them.
Activate customers: Build playbooks for onboarding and driving employee participation.
Remove friction: Spot blockers early (messaging, HR Ops, timing) and clear them.
Grow usage → grow accounts: Work with HR Ops/Comms to roll out benefits, send emails/SMS, run webinars, and increase adoption.
Drive renewals + expansion: Create QBR and renewal templates tied to budget cycles; help convert pilots (ex. clinical) into bigger rollouts (ex. all-staff).
Connect the dots internally: Loop between Sales, CS, SDR, Product, and RevOps so everyone sees the same picture.
Enable the team: Coach Account Management on renewal and stakeholder politics; help SDR tighten messaging (quality > volume).