TLC Careers

Current Opportunities

Enterprise Account Executive

Job Location: Remote (U.S. based) with required travel to Boston 4 times annually

Type: Full-time

ABOUT THE ROLE

You'll be creating and developing enterprise pipeline into meaningful, durable revenue. You'll own the sales cycle from securing the first conversation through delivering signed contracts, primarily with senior HR, Talent, and Learning leaders at large enterprise organizations. Our enterprise engagements typically range from $200K to $400K+.

You'll work closely with our Head of Marketing, who is building the account-based marketing strategy, inbound engine, and demand generation infrastructure that will help create and accelerate pipeline. This is a true partnership: Marketing will help identify and engage the right accounts, in addition to your own outbound efforts; you'll turn that interest into relationships, opportunities, and closed business.

You'll report directly to the CEO and work closely with TLC's leadership team and founders. You'll have genuine access, fast feedback, and significant influence over how we go to market. We're looking for someone who sees that proximity and visibility as an opportunity to build, learn, and have outsized impact.

This is not a role for someone looking to inherit a mature sales machine. We have a leadership development offering that works and strong relationships with some of the world's most respected companies. Now we need someone who can help us build a repeatable and predictable enterprise sales motion around it.

WHAT YOU'LL OWN

• New enterprise revenue. Own the full sales cycle across new accounts, from discovery and qualification through stakeholder alignment, proposal, negotiation, procurement, and close.

• Outbound prospecting and pipeline creation. Proactively create new enterprise opportunities through thoughtful, targeted outreach, relationship building, referrals, and other prospecting efforts. Marketing will be an important partner in generating demand, but you’ll also own building pipeline yourself and opening doors into priority accounts.

• Complex enterprise relationships. Build credibility with senior HR, Talent, and Learning leaders and navigate the multiple stakeholders involved in significant leadership development investments.

• Pipeline progression. Using a methodology like MEDDPIC, create momentum across opportunities, identify what's blocking a deal, and consistently drive toward a clear next step.

• Partnership with Marketing. Work closely with our Head of Marketing on target accounts, messaging, outreach, campaigns, and the feedback loops that make both sales and marketing better.

• Pipeline discipline and forecasting. Maintain a clear, accurate view of opportunities, next steps, risks, and expected revenue in HubSpot.

• Our evolving sales playbook. Bring what you're learning from buyers back into the business and help sharpen our positioning, qualification, sales process, and overall go-to-market approach.

MUST HAVE

• Enterprise HR buyer experience. You've successfully sold to CHROs, Chief People Officers, VPs of Talent, Learning & Development leaders, or similarly senior HR buyers at large organizations.

• Pipeline generation. You’ve demonstrated the ability to create your own enterprise pipeline through targeted outreach, relationship building, referrals, and other prospecting efforts. You’re comfortable generating new opportunities yourself, not just converting marketing-generated leads.

• A record of closing meaningful enterprise deals. You've personally closed complex, multi-stakeholder deals of $200K+ and know how to navigate procurement, legal review, executive stakeholders, and long sales cycles.

• A track record of results. You've consistently carried a meaningful enterprise quota and can point to a history of meeting or exceeding it.

• Experience operating in a build environment. You're comfortable without a fully established playbook and have helped shape or improve the sales motion around you.

• A genuine connection to the work. You're excited by the opportunity to help organizations develop better leaders, and that interest shows up in the choices you've made and the work you've pursued.

HIGHLY VALUED

• Experience as a sole or primary quota carrier at a small company or scale-up

• Experience selling leadership development, executive education, coaching, L&D, HR technology, or another high-consideration people solution

• A strong network among senior HR, Talent, or Learning leaders

• Experience helping build or evolve an enterprise sales motion

• Experience at a company with fewer than 150 employees

• 8–12 years of relevant experience

• Familiarity with HubSpot and modern sales tools

SKILLS & STRENGTHS

• Exceptional discovery and consultative selling. You ask smart questions, listen closely, uncover the real business problem, and connect it to a compelling solution.

• Executive presence. You build credibility with senior leaders through clarity, confidence, curiosity, and good judgment. You know how to be persuasive without overselling.

• Commercial judgment. You know where to spend your time, distinguish genuine buying signals from polite interest, and understand what it will take to move an opportunity forward.

• Relationship building and influence. You build trusted relationships and navigate multiple stakeholders, priorities, and perspectives across a complex organization.

• Ownership and execution. You create momentum, follow through relentlessly, stay organized and documented across a complex pipeline, and take responsibility for outcomes.

• Builder and collaborator. You share what you're learning, make the people around you better, and enjoy turning what works into repeatable practices. You're comfortable testing, learning, and adjusting as TLC's go-to-market motion evolves.

WHAT SUCCESS LOOKS LIKE

• In your first 90 days: You've developed a deep understanding of TLC's programs, customers, buyers, and competitive landscape. You know the existing pipeline account by account, have established credibility with active prospects, and are creating measurable forward movement on priority opportunities. You've also developed a clear point of view on where TLC is most likely to win and what will help us win consistently.

• By the end of year one: You've made a meaningful contribution to new enterprise revenue and built a healthy pipeline for continued growth. Just as importantly, you've helped TLC understand what repeatable enterprise selling looks like here: who we win with, why we win, how we move opportunities forward, and what sales infrastructure we need to scale.

How to Apply

If you're interested in this opportunity, please email careers@tlcleaders.com with the following:

• A link to your LinkedIn profile

• Your resume

• A brief description of the most complex enterprise deal you've closed including ACV, number of stakeholders, how long it took, and what you did to get it across the line. No cover letter needed. That story is enough.

We look forward to hearing from you!

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