Leland’s mission is to unlock human potential by making the world’s expertise more accessible. Our platform connects ambitious people with coaching, content, and courses that can can help them achieve their career and educational goals. Since our founding in 2021, we’ve helped tens of thousands of people reach their most ambitious goals, raised $19M from world-class investors, and built the industry leader in educational, career, and AI coaching.
Leland is hiring its first-ever Head of Sales to own, lead, and build our entire revenue organization, spanning both our B2B business and our consumer sales motion. This is a player-coach role: you will take demos and close deals with employers and universities, hire and train a team of B2B reps, and lead a consumer sales team selling coaching packages and bootcamps directly to individuals.
You will work directly with the leadership team to shape Leland's go-to-market strategy, and you will own the full revenue lifecycle: net new business, onboarding, renewals, and expansion.
This role is right for someone whose scope has grown at every stage of their career. You've been a top performer. You've built and led a team. You understand what great looks like from every seat in a sales org. You'll define how we sell, who we hire, and what winning looks like for years to come.
ResponsibilitiesSell
Carry a personal book of business and own the most complex, high-value deals across our employer and university verticals
Take demos, run discovery, and close contracts, serving as the senior presence in high-stakes sales conversations
Work cross-functionally with Growth, Product, and Operations to convert pipeline and refine how Leland is positioned in the market
Set strategy and direction for Leland's consumer sales motion, coaching the team toward consistent performance across product lines with varying margin and volume profiles
Design and document Leland's end-to-end B2B sales process, from initial outreach through close and handoff to Account Management
Build and own our Sales Operations infrastructure: CRM hygiene (HubSpot), pipeline reporting, forecasting, and performance dashboards
Develop playbooks, training materials, and onboarding frameworks that will enable future hires to ramp quickly
Establish rules of engagement, compensation philosophy, and quota-setting approach as the team grows
Build and hire a high-performing sales team as business growth justifies expanding headcount
Lead a growing sales organization across both B2B and consumer channels, including direct reports on the B2B side and oversight of a consumer sales team and their manager
Set clear expectations, coach to outcomes, and provide hands-on mentorship
Build a culture of accountability, rigor, and high-performance on the sales team
8+ years of B2B sales experience, with clear progression from individual contributor to sales leader in a high-performing sales organization
Demonstrated success selling to employers, corporations, and/or universities: you understand how decisions get made at each type of organization
Experience building or significantly contributing to sales operations: CRM management, pipeline reporting, forecasting, and territory design
Has built and led sales teams in a startup or growth-stage environment, ideally across multiple stages of scale
A genuine player-coach mentality: excited about carrying a bag alongside managing the team, not just directing from the sideline
Exceptional communication and presence; comfortable selling to and influencing senior stakeholders and executive buyers
Based in Lehi, UT or willing to relocate; this is a full-time, in-office role
The chance to join a world-class team helping people achieve their career and educational dreams
Work in a collaborative, high-energy environment where your contributions have a direct impact
Operate in a fast-paced, AI-native environment
We don't hire people who merely want to work for a great company; we hire people who want to make a great company
Leland is an equal opportunity employer. We encourage candidates of all backgrounds and demographics to apply.
Skills Required
- 8+ years of B2B sales experience with progression to sales leader
- Demonstrated success selling to employers, corporations, or universities
- Experience building sales operations with CRM management and pipeline reporting
- Built and led sales teams in startup or growth-stage environment
- Exceptional communication skills for selling to senior stakeholders
What We Do
Leland is a coaching marketplace that provides access to coaching, content, and courses to help individuals achieve their career and educational goals.
