Head of Customer Success

SideShiftNYC-HQCustomer Success

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Opens the official SideShift careers page

Salary

Not listed

Job type

Full-time

Posted

30 Sept 2026

Status

Open · checked 7d ago

About this role

SideShift seeks a Head of Customer Success for its New York headquarters to lead and scale the customer success organization. This full-time, in-person position suits an experienced B2B SaaS professional eager to build an AI-native department from the ground up.

Role Overview

SideShift is looking for a strategic leader to direct customer onboarding, adoption, retention, and expansion for a rapidly growing global user base. This unique leadership opportunity treats artificial intelligence as the core operating model rather than an afterthought. The chosen candidate acts as an operator, builder, and coach who designs workflows, integrates advanced tooling, and stays close to strategic accounts to ensure measurable value delivery.

Key Responsibilities

Own the end-to-end customer journey from initial onboarding through contract renewals and account expansion.

Establish the Customer Success department by creating foundational playbooks, operational processes, key metrics, and internal tooling.

Construct an AI-native team by deploying agentic artificial intelligence to automate workflows, uncover insights, and predict customer risks and opportunities.

Acquire a comprehensive understanding of client objectives to formulate tailored strategies that drive platform adoption and ongoing growth.

Cultivate strong relationships with key clients and personally oversee strategic accounts when necessary.

Establish direct feedback loops connecting the customer base with Product, Sales, and Engineering teams to influence company priorities.

Requirements

Possess five to ten years of professional experience, featuring significant Customer Success tenure within a B2B SaaS enterprise.

Demonstrate a proven capability to build or substantially enhance a Customer Success function, operating model, or playbook from the ground up.

Operate as an AI-native professional who actively utilizes agentic AI in daily tasks and envisions automated workflow transformations.

Apply first-principles thinking centered on the core objective of ensuring clients successfully realize the value of their purchase.

Exhibit robust commercial and analytical instincts backed by a track record of driving adoption, retention, and revenue expansion.

Display high-ownership execution, exceptional communication skills, and the ability to thrive in ambiguous environments.

Skills and Tools

Customer Success Management

B2B SaaS Operations

Playbook and Process Development

Agentic Artificial Intelligence Tooling

Workflow Automation

Strategic Account Management

Data Analytics and Commercial Strategy

Cross-functional Collaboration

Salary and Benefits

On-Target Earnings (OTE) ranging from $175,000 to $225,000, calibrated according to individual experience and scope.

Equity compensation included.

About the Company

SideShift develops the operating system for the creator economy, facilitating brand campaigns, authentic creator video production, matching, tracking, and payouts. The company operates out of a headquarters in New York City with an in-person schedule of five days per week. SideShift supports over one million creators and three thousand brands, having paid out more than $100 million to creators to date. The organization features investors and board members such as Reid Hoffman.

How to Apply

To apply for this position, please visit the official company careers page.

Questions candidates ask

Where is the Head of Customer Success role located?

The position is located at the company headquarters in New York City and requires working in person five days a week.

What is the salary or OTE for this position?

The On-Target Earnings (OTE) range from $175,000 to $225,000, along with equity, and is calibrated based on experience and scope.

What background is required for this role?

Candidates need 5 to 10 years of experience, which must include significant Customer Success background at a B2B SaaS company and experience building a CS function from scratch.

What does SideShift do as a company?

SideShift builds the operating system for the creator economy, enabling brands to run campaigns and creators to make product videos while handling matching, tracking, and payouts.

What does an AI-native customer success approach mean for this job?

It means using agentic artificial intelligence as the operating model to automate workflows, surface insights, and proactively identify risks and opportunities rather than relying on a headcount-heavy team.

Ready to apply?

The application is on the official SideShift careers page.

Apply on company site