Customer Success Operations Lead

(Hybrid in NYC)

Our client Boomerang is on a mission to revolutionize how employers stay connected with their former colleagues. We believe relationships matter and are here to provide a simple, affordable, and automated solution that keeps those connections alive. 

We are a seed-stage company (~ $12M in venture capital from Tier 1 funds) that has assembled some of the best builders, designers, and product minds to reimagine the future of work.

We're seeking a CS Ops Lead to join our New York office as one of our first twenty hires. This is an opportunity to join us on the ground floor, working alongside seasoned founders with a track record of successful companies.

About the role

You'll be a senior, player-coach Operations leader responsible for effectively launching and scaling our Enterprise Customer Success function from the ground up with a strong focus on data. Based in our NYC office, you'll build the infrastructure, processes, and playbooks that take CS from "V1" to a repeatable, scalable operation—while staying close to the work and partnering day-to-day with a high-performing IC who is strong in direct client relationships. This role blends strategic leadership with hands-on execution: you'll identify, strategize and support key customer conversations, drive support and success outcomes, and become the internal expert on CS data—building and improving reporting and BI dashboards, translating customer and operational needs into clear requirements for Engineering, and automating what's currently manual so the team can scale sustainably.

What you'll be doing

• Launch and scale the Enterprise Customer Success function—design the operating cadence, playbooks, and core processes (onboarding, support-to-success workflows, QBRs, renewals, escalation paths) and evolve them from "V1" to repeatable "V4" systems.
• Partner closely with an existing client-facing IC to "tag-team" enterprise accounts—joining key calls, shaping account strategy, providing data-backed storytelling, and ensuring customers receive both strong day-to-day support and proactive success guidance.
• Own CS data and reporting end-to-end: build and maintain BI dashboards, unblock reporting needs, and become the internal expert who can quickly answer questions and surface insights (including working in the weeds with SQL/BI tooling).
• Translate customer pain points and workflow gaps into crisp requirements for Engineering—articulate what needs to be built or improved to make support/success more scalable and less manual.
• Identify and automate high-friction, manual CS workflows (intake, triage, reporting, customer updates, internal handoffs) so the team can scale without adding unsustainable overhead.
• Lead and coach as a player/coach—setting priorities, creating clarity during fast-moving days, and helping the broader team step back from constant firefighting through better process and cross-functional alignment.
• Drive strategic customer outcomes at the enterprise level—building onboarding plans, coordinating stakeholders, and ensuring customers realize value quickly and consistently.

What we're looking for

• Proven experience leading or helping launch an Enterprise Customer Success function in a growing company—building the foundations (playbooks, workflows, cadences, success plans) while still owning day-to-day execution
• Startup Operations experience, leveling up functions, scaling impact, etc.
• Player/coach mindset: comfortable partnering closely with a strong client-facing IC, jumping on customer calls as needed, and providing strategic direction without needing to be "the hero"
• Exceptional data fluency—you can get into the weeds, write "loose" SQL, and build BI dashboards (e.g., Amazon QuickSight) to create reliable reporting and customer health visibility
• Track record of turning manual, ad hoc reporting into scalable processes through automation, clean definitions, and repeatable metrics that unblock the team
• Strong cross-functional partner who can translate customer needs into clear requirements for Engineering/Product, and help prioritize improvements that make Support + Success more effective
• Highly process-oriented and systems-minded: able to move the org from "V1 to V4" by iterating, documenting, and continuously improving how work gets done
• Comfortable operating in a fast-paced startup environment—able to handle ambiguity, prioritize effectively, and balance fire-fighting with longer-term infrastructure building
• Customer-first, enterprise-caliber communication skills: able to drive executive-ready QBRs/updates, manage escalations, and build trusted relationships across stakeholders
• No-ego, hands-on leadership style—strategic and thoughtful, but equally willing to do the "grunt work" to launch and stabilize the function

What you'll need

• Dynamic startup operations experience (esp. cross-functional process driving experience)
• Proven experience in enterprise Customer Success (support + success), including leading renewals/expansions, driving adoption, and managing escalations with senior stakeholders
• Hands-on strength in data and reporting—comfortable working with SQL and building/maintaining BI dashboards (e.g., Amazon QuickSight or similar) to unblock reporting and make performance measurable
• Ability to translate customer and CS needs into clear, actionable requirements for Engineering/Product, and partner closely to improve workflows and tooling
• Demonstrated success building CS infrastructure from scratch or taking a function from early-stage "V1" processes to scalable, repeatable playbooks
• Strong process orientation with a bias for automation—able to identify manual work, design better systems, and implement improvements without waiting for perfect conditions
• Player-coach mindset: comfortable leading by example, staying customer-facing, and supporting/mentoring an IC while also owning strategic work
• Comfort operating in a fast-moving startup environment—low ego, collaborative, and willing to jump into execution when needed
• Ability to work from the NYC office (in-person role)

What this specific role offer

• The chance to launch and shape an enterprise Customer Success function—own the playbook, processes, and operating rhythm from day one and evolve it from "V1" to "V4."
• A high-impact, visible role partnering closely with leadership and cross-functional teams (especially Engineering) to improve the customer experience and scalability of support + success.
• Meaningful ownership of data and reporting, with the mandate to streamline manual work, build reliable dashboards, and make customer health and outcomes easy to see and act on.
• A player/coach environment: lead and develop a strong customer-facing IC while staying hands-on with key accounts and strategic work.
• An in-office NYC team setting, with close collaboration, quick feedback loops, and the ability to get into the details and drive change fast.
• Room to grow your scope over time, with pathways to broaden into adjacent areas like customer experience and go-to-market collaboration as the team scales.

Flexibility and Logistics:

Location 

New York, New York

Compensation

$120,000 - $140,000 USD + equity (we're still confirming balance between base / a potentail bonus component and will confirm with candidates directly once we're settled here. This range is our best estimate right now)

How We Work

We’re not a 9-to-5 company. We push hard when the work demands it and give each other space when it doesn’t. Our culture is grounded in trust and accountability. Our co-founders are seasoned entrepreneurs who know building a company is a marathon, not a sprint. We care deeply about what we’re building  and the people building it.