Head of Sales Enablement

Front is the leading AI-powered customer service platform built for collaboration. Front brings core support channels into a modern, intuitive workspace where teams can collaborate on requests, automate manual processes, and delight customers across their entire lifecycle. Front’s flexible workflows, AI features, and customer intelligence provide the efficiency and insights to keep entire organizations customer-first, every day. More than 9,000 of the most innovative companies worldwide including CultureAmp, HootSuite, and Y Combinator use Front to deliver five-star service at scale.

Backed by Sequoia Capital and Salesforce Ventures, Front has raised $204M from leading venture capital firms and independent investors including top executives at Atlassian, Okta, Qualtrics, Zoom, and PagerDuty. Front has received numerous Great Place to Work accolades, including Built In's 100 Best Midsize Places to Work in SF 2025, Y Combinator's list of Top Companies in 2023, #4 on Fortune’s Best Workplaces in the Bay Area ,Inc. Magazine's 2022 Best Workplaces list, and Forbes Best Startup Employers 2022 List.

As the Head of Sales Enablement, you will build and lead Front's global sales enablement function, driving strategic initiatives that accelerate revenue growth and sales excellence across our GTM organization. In this role, you will serve as the critical connection point between Sales, Product, and Marketing organizations. This role requires a strategic leader who can orchestrate alignment across these functions to ensure consistent messaging, product positioning, and go-to-market execution.

What will you be doing?

• Strategic Leadership & Team Building: Build and lead a best-in-class enablement team, including hiring, developing, and managing enablement professionals.

• Sales Excellence & Performance Optimization: Design and implement advanced sales methodologies and frameworks that drive consistent sales execution.

• Program Development & Innovation: Architect a comprehensive enablement curriculum including role-specific onboarding, ongoing training, and advanced selling techniques.

• Cross-Functional Leadership: Partner with Product Marketing to develop sophisticated product positioning and competitive strategies.

What skills and experience do you need?

• 8 years of progressive experience in sales enablement, with at least 3 years in a leadership role.

• Experience managing and developing teams of 5 enablement professionals.

• Proven track record of building and scaling enablement functions in high-growth SaaS companies.

• Strong business acumen with experience in sales strategy development and execution.

• Track record of successful partnership with C-level executives and senior leadership teams.

• Deep understanding of enterprise sales methodologies (MEDDIC, Challenger, Solution Selling, etc.).

This is a hybrid role, expected to be in our Chicago office on Tuesdays and Thursdays.

What we offer

• Competitive salary

• Equity (we are post-series D & backed by some of the best VCs in the US)

• Private health insurance, including plan options at no cost to employees

• Paid parental leave

• Flexible time off policy

• Focus Fridays - learn more here!

• Flexibility to work from home 3 days/week (unless posted as a full-remote role)

• Mental health support with Workplace Options

• Family planning support with Maven

• $100 per month Lifestyle Stipend to spend on fitness, health and wellness, and other activities

• Wellness Days - Fronteers get an additional day off on months with no holidays

• Winter Break - Our offices are closed from Christmas to New Year's Day!

Front provides equal employment opportunities (EEO) to all employees and applicants for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, age or disability. By applying, you acknowledge and agree that you have read and understand the California Recruiting Privacy Notice & EU Privacy Notice

Compensation Range: $169K - $200K