Fractional Sales Manager

TL;DR

Fractional Sales Manager (SaaS/Edtech): Design and refine sales strategy and product requirements for selling annual subscription-based packages to Fortune 1000 companies with an accent on building repeatable processes and providing sales coaching to enterprise team. Focus on establishing scalable methodologies, performance metrics, forecasting, and team structure for sustainable revenue growth.

Location: Must work from Canada or anywhere in the US (except California). Remote 100%.

Company

Remote-first company (HQ Toronto, Canada, established 2007) offering software conferences and online learning products.

What you will do

• Partner with leadership to design repeatable sales processes and identify product features for selling annual subscription seat packages to Fortune 1000 companies.
• Mentor enterprise sales team on lead gen, consultative selling, relationship-building, and negotiation.
• Introduce sales methodologies, set strategy, define metrics, and establish forecasting.
• Participate in pipeline reviews, deal strategy, and alignment with marketing, BD, and customer success.
• Shape hiring profiles, onboarding, and team structure for sales growth.
• Occasionally attend virtual client meetings to model best practices.

Requirements

• 6+ years selling annual subscription-based packages for learning platforms to Fortune 1000 companies in USA; 3+ years sales leadership (direct reports)
• 2 of last 3 years selling SaaS/subscription/enterprise software to Fortune 1000 in USA
• Proven coaching, team scaling, complex enterprise deals, and executive communication.
• Proficiency in HubSpot, Apollo, Zoom, Google Docs, Wrike.
• 10-15 hours/week; daily availability 9am-1pm ET; weekly team calls
• Professional home office with fast internet and recent computer (<4 years old)

Culture & Benefits

• Remote-first and remote-always since 2007.
• Prioritize respect, fairness, support, well-being, and core values.
• Encourage diversity, equity, inclusion; safe environment for all.