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Open nowPosted 26 days ago

Head of Customer Success

SideShift7 open roles

Where
NYC-HQ
Work mode
On site
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Your applicationOpen nowHead of Customer SuccessSideShift · NYC-HQ

  1. YouYes, apply to this one.

  2. CV RocketCV written for this posting.

  3. 25 readersRecruiter, hiring manager, skeptic. Round after round.

  4. CV RocketApplied on SideShift's own form.

The reply lands in your private mailbox

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The clock on this job

Early applications get read.

12.3% of postings close within 7 days. Measured by our own scanner across the market.

Share of postings closed within
  1. 2.1%1 day
  2. 4.5%3 days
  3. 12.3%7 days
  4. 19.3%14 days
  5. 35.6%30 days
  6. 58.1%60 days
This job: posted 26 days ago

The posting

SideShift is building the operating system for the creator economy: brands run campaigns, creators make authentic product videos, and the platform handles matching, tracking, and payouts.

We’re ~20 people, ~2 years old, and growing fast: revenue roughly 3× last month and ~10× over the last 6 months. More than 1M creators and 3,000+ brands use SideShift; $100M+ has been paid out to creators. If you’ve seen social groundswell around brands like Cursor, Suno, or Dr. Melaxin, that content often started here.

This is not a traditional Head of Customer Success role. We’re looking for a leader who treats AI as the operating model for customer success – not a bolt-on. You’ll own adoption, retention, and expansion across our growing global customer base, and you’ll build a CS function that is AI-native from day one: leaner, faster, and more proactive than a headcount-heavy team could ever be.

You’ll be equal parts operator, builder, and coach. You’ll design the playbooks, wire up the AI tooling that runs behind them, hire and develop the team, and stay close enough to our most strategic customers to know exactly where value is being won or lost.

WHAT YOU'LL DO

- Own the customer journey from onboarding through renewal and expansion, with a focus on delivering meaningful, measurable value to customers.

- Develop the Customer Success function, including creating playbooks, processes, tooling, metrics, and more.

- Build an AI-native CS organization, using agentic AI to automate workflows, surface insights, proactively identify risks and opportunities, and dramatically increase the leverage of the CS team.

- Develop a deep understanding of customers’ businesses, goals, and workflows and translate that understanding into strategies that drive adoption, retention, and growth.

- Build strong relationships with key customers, proactively identify risks and opportunities, and personally manage strategic accounts when needed.

- Create tight feedback loops across Product, Sales, and Engineering, ensuring customer insights inform company priorities and product development.

WHAT YOU'VE DONE

- 5–10 years of experience, including significant Customer Success experience at a B2B SaaS company.

- Demonstrated ability to build or materially improve a Customer Success function, playbook, or operating model from scratch.

- AI-native operator who actively uses agentic AI in their day-to-day work and is excited to rethink how Customer Success operates when AI agents can own meaningful parts of the workflow.

- First-principles thinker who focuses on the fundamental goal of Customer Success: ensuring customers realize the value they purchased.

- Strong commercial and analytical instincts, with experience driving adoption, retention, renewals, and expansion.

- High-ownership operator and exceptional communicator who thrives in ambiguity and can move fluidly between strategy, customer relationships, and hands-on execution.

INTERVIEW PROCESS

1. Initial conversation with our recruiting team

2. Conversation with Chris Brantley, Head of Strategy and Operations

3. Conversation with Canyon Pergande, Co-founder and COO

4. Onsite interviews with Nick Lawton, CEO, Drew Levin, CTO, and more.

5. References + offer

Location: New York City, in person 5 days/week OTE: 175,000–225,000 + equity, calibrated to your experience and scope.

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One press. We do the rest.

  1. A CV for this posting

    Written against SideShift's own wording, from every piece of relevant proof in your profile.

  2. 25 readers review it

    Recruiter, hiring manager, skeptic and more read every draft, round after round. You get the best round.

    The review screen in CV Rocket: how each CV was read, round by round.

  3. We apply on SideShift's form

    Our application engine gets through the hardest forms there are. Where a question needs you, AI suggests the best answer. Don't want us applying from our IP addresses? Use our Chrome extension: we apply straight from your own browser.

    An application in CV Rocket: every answer filled in on the employer's form.

  4. Every reply, sorted

    SideShift's answer lands in your private mailbox, and we classify it on arrival: interview, question, rejection.

    The CV Rocket inbox: each employer reply classified as an interview, an action or a rejection.

  5. Reply with AI

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  6. The interview in your calendar

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    An interview invitation in the CV Rocket inbox, added to the candidate's calendar.
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