[Remote] Sales Manager

Note: The job is a remote job and is open to candidates in USA. Winning.Careers is building an AI-powered platform that connects students, alumni, and institutions to real-world expertise. They are seeking a Sales Manager to lead B2B sales efforts targeting higher education institutions, helping to build the sales function and establish relationships with decision-makers at universities and private schools nationwide.

Responsibilities

• Own the entire B2B sales cycle from prospecting to close, building a pipeline of university and private school clients
• Develop and execute a territory plan targeting 3,000+ institutions in Year 1
• Build relationships with Deans of Career Services, and VP-level decision-makers
• Conduct compelling product demonstrations and articulate ROI to procurement committees
• Negotiate contracts and navigate complex institutional buying processes
• Collaborate with the CEO and leadership team to refine messaging and sales strategy
• Document learnings and contribute to the development of repeatable sales playbooks
• Represent Winning.Careers at industry conferences and networking events

Skills

• 2+ years of B2B sales experience, preferably in EdTech, SaaS, or higher education
• Proven track record of closing six-figure annual contract values
• Experience selling to higher education institutions and navigating procurement processes
• Self-starter mentality with the ability to thrive in a 100% commission environment
• Excellent communication, presentation, and negotiation skills
• Comfort with technology and ability to demonstrate software platforms
• Experience selling PeopleGrove, Handshake, Symplicity, Graduway, or similar platforms
• Existing relationships within university career services or advancement offices
• Understanding of the higher education technology landscape
• Startup experience and comfort with ambiguity
• Bachelor's degree or equivalent experience

Benefits

• Equity Grant: 0.5% fully diluted equity (vesting over 4 years with 1-year cliff)
• Accelerators: Earn 35% commission on all deals closed after exceeding annual quota
• Spiff Bonuses: $2,500 bonus for first deal closed; $5,000 bonus for hitting quarterly targets
• Expense Account: Monthly budget for travel, client entertainment, and conference attendance
• Flexible Schedule: Work remotely with autonomy to manage your territory

Company Overview