Enterprise Account Executive

Woolf • IL

71d

About The Position

Woolf is looking for a dynamic, results-driven Account Executive (Independent Contractor) to play a key role in our global expansion. As part of our team, you'll lead the charge in acquiring new customers and growing Woolf’s footprint in the education sector. This role offers the unique opportunity to shape the future of education by working closely with innovative education organizations. To be successful, you'll engage in full-cycle sales, from prospecting to closing deals, using a consultative approach to demonstrate how Woolf’s platform addresses their specific needs. Reporting to the Head of Sales, you’ll be able to collaborate with a diverse team of academics, product specialists, and engineers to accelerate Woolf’s growth.

Requirements

• 5–8+ years of B2B enterprise sales experience in SaaS, EdTech, or accreditation/compliance-related industries.
• Proven track record of closing large, multi-stakeholder deals ($100K–$1M+ ARR).
• Strong consultative selling and negotiation skills.
• Experience with long, complex sales cycles and multiple buyer personas.
• Exceptional written and verbal communication skills.
• Ability to build credibility with executive, technical, and academic audiences.
• Familiarity with CRM tools (Salesforce), account planning, and sales methodologies.

Nice To Haves

• Experience in EdTech or a strong understanding of the education sector.
• Experience in a start-up as a founding Enterprise AE.

Responsibilities

• Pipeline development & account planning.
• Manage complex sales cycles with multiple decision-makers and long procurement processes (6–18 months).
• Maintain accurate and updated deal stages, forecasts, and next steps in CRM.
• Provide regular pipeline reports, risk assessments, and win/loss feedback to leadership.
• Partner closely with marketing to refine messaging, case studies, and go-to-market strategy.

Benefits

• Flexible, fully remote work environment.
• Flexible PTO and working hours.
• New hire stipend for home office setup.
• Health insurance, 401(k) with company match.

What This Job Offers

• Career Level: Mid Level