Founding Account Executive

Founding Account Executive

Location: Mostly Remote, but with work-related travel ~monthly (U.S.-based)
Reports to: Senior Leadership

About CareerVillage.org

CareerVillage.org is a fast-scaling tech-startup-style nonprofit at the intersection of education, equity, and technology. We believe everyone deserves access to high-quality career guidance. That’s why we’ve built Coach, an AI-powered career navigation tool designed to help learners and job-seekers reach their full potential.

We’re looking for a Founding Account Executive to lead and scale the next phase of our go-to-market motion for Coach. You’ll design the system that makes our growth repeatable, efficient, and data-informed. You’ll blend strategy and execution by refining our segmentation, pricing, and playbooks while driving anchor deals that bring Coach to large numbers of learners and set us up for scaled deployments.

About the Role:

You’ll lead CareerVillage’s business development efforts across our core markets in workforce development and higher education. You’ll own both go-to-market (GTM) strategy and pipeline performance, including targets for deal volume, partner launches, and the number of learners we reach through those partners, while building the processes, playbooks, and tools that reduce cycle time, improve conversion rates, and strengthen impact storytelling.

You’ll work closely with our CEO, Product, Marketing, and Partner Success teams to shape how we present Coach to institutional buyers and partners. This role is part strategist, part operator. You’ll spend as much time in discovery calls and demos as you will in refining our GTM system for scale.

This is a fit for an entrepreneurial, analytical, and mission-driven builder who can translate insight into action. You’ll move fluidly between executive-level negotiations, data-driven experimentation, and coaching your sales team to excel.

What You’ll Do:

As our Founding Account Executive, you will:

• Own top deals: Lead discovery, demo, negotiation, and contracting for high-value partnerships that anchor our GTM strategy.
• Build and manage the pipeline: Oversee outreach, qualification, and forecasting. Maintain strong Salesforce discipline and ensure consistent visibility into performance metrics, with a focus on growing the number of active partner deployments and learners using Coach through those partners.
• Spearhead the sales motion: Set weekly cadences, coach on discovery and objection handling, and model commercial excellence through hands-on selling.
• Integrate AI and automation: Leverage AI to improve productivity, accelerate research, and test new approaches to prospecting and engagement.
• Run rapid market experiments: testing segments, messaging, target profiles, and partnership models, then codify what works into clear, repeatable playbooks that reveal where the strongest traction exists.
• Collaborate cross-functionally: Partner with Product, Engineering, and Impact teams to feed insights from the field back into the roadmap, messaging, and evidence-building.
• Measure and optimize performance: Track conversion, cycle time, CAC, ROI, and scale metrics such as partners launched and active learners per deployment. Use data to guide resourcing and prioritize opportunities.
• Drive GTM strategy: Help define market segmentation, ICPs, pricing logic, and value propositions across key buyer segments (job training, higher ed, corporate L&D). You’ll help decide where we bet next (by segment) and design experiments to prove or disprove those bets.
• Guide/Develop assets: Partner with Impact and Marketing to create early case studies, ROI models, and success narratives that drive credibility and scale.

Example Customer Profiles:

CEOs or program directors of job training orgs with short-duration training programs, directors of career services at higher ed colleges and universities, and other related customers.

About You:

We know no candidate will meet 100% of the qualifications. We value lived experience and transferable skills as much as formal experience. That said, the strongest candidates will bring:

• Have previous startup experience (ideally early stage but at a company you brought above $1M ARR)
• 6-8 years of hands-on execution style experience in business development, partnerships, or sales, ideally in the tech sector or the workforce innovation.
• Experience as an entrepreneurial sales leader with past experience as a zero-to-one or founding account executive, skilled at experimenting across markets to find traction and shape our go-to-market path.
• Proven ability to experiment across markets with a builder’s mindset, shaping and refining GTM systems in ambiguous, high-opportunity environments where no finished playbook exists.
• Commercial rigor: you can talk pipeline math, pricing, payback periods, and win rates with confidence.
• Accountability for hard numbers: you’ve previously been on the hook for concrete targets (e.g., deals closed, accounts launched, or users activated).
• Technical fluency - you can demo AI products, discuss integrations or APIs with technical stakeholders, and translate technical features into business value.
• Data-informed storytelling - you pair narrative with measurable outcomes and know how to build referenceable pilots that scale.
• Mission alignment - you care about equity, career mobility, & using tech for social impact.

Also nice to see but not necessary:

• Have experience building partnerships in the workforce, learning, or tech ecosystems, but please do not hesitate to apply if you do not have direct experience in these sectors.
• Cross-segment fluency - you’re comfortable pivoting between higher ed, tech partners, corporate L&D, and job training providers.
• Have run pilots that moved from discovery to expansion, or built early revenue engines in growth-stage organizations
• Bring consulting, sales ops, or RevOps experience that strengthens your ability to design systems, not just execute them
• Leadership - you’ve hired, coached, or managed BDRs or AEs, and built a performance-oriented, learning-driven culture. You’re excited to help hire and shape a small, high-output BD pod here.

What We Offer:

• A mission-driven team environment where your work makes a real impact
• Remote-first flexibility, with some travel for conferences and convenings
• Salary range; FTE: This is a full-time, exempt role with a base salary range of $95,000 to $105,000, plus performance-based variable compensation. On-target earnings (OTE) range up to $145,000, based on a 70/30 base-to-variable split (70% base, 30% variable). Total OTE for this role does not exceed $145,000.

Note: Compensation is dependent on experience, location, and alignment with the role requirements.

• Benefits:
• Healthcare and dental benefits
• 401K matching
• $1,500 annual professional development budget
• Generous vacation and wellness policies
• Note: CareerVillage is an at-will employer. New hires will begin with a two-month introductory period designed to ensure mutual fit and provide onboarding and feedback.

Location:

We are a remote-first organization and can hire for this role from the following states in the USA:

Alabama, Arizona, California, Colorado, Florida, Georgia, Hawaii, Idaho, Illinois, Indiana, Maryland, Massachusetts, Montana, New Hampshire, New Jersey, New Mexico, New York, North Carolina, Oklahoma, Oregon, Pennsylvania, Texas, Utah, Virginia, and West Virginia. Hybrid is optional in NYC. CareerVillage has team members worldwide. HQ is in Palo Alto, CA.

CareerVillage.org is an equal opportunity employer.

CareerVillage is an equal opportunity organization that celebrates diversity (for more information about our approach, check out our Diversity, Equity, and Inclusion Guidelines). Diversity includes race, gender identity, age, national origin, disability status, size, religion, sexual orientation, parental status, socioeconomic background, and many other parts of an individual’s identity. We are a fair-choice employer for qualified applicants with a history of arrest or conviction. All are welcome to apply and will be considered for this role. Each team member’s perspective is integral to our success, and fostering an inclusive environment is everyone’s responsibility. At this time, we can only consider applicants with authorization to work in the United States on a permanent, full-time basis; unfortunately, we cannot provide visa sponsorship.