Purpose
Every connection we facilitate has meaning—Experts find fulfillment in shaping future generations while Vanguards discover their true career calling
JOIN OUR MISSION
Shape the Future of Career Services
We're building the Operating System for Career Services—an AI-powered platform connecting students with real-world expertise. Join our venture-backed team and make a meaningful impact.
Our Mission
To Bridge The Gap Between Ambitious Individuals & Specialized Knowledge, Enabling Informed Career Decisions At Critical Junctures
Passion
We believe in the transformative power of human connection and the fire that ignites when ambition meets wisdom
Precision
We deliver the right expertise at the right moment through structured, professional interactions that respect everyone's time and goals
Open Positions
Join our team and help transform career services
Part-Time • Remote
Operations Intern
Gain Real-World Experience at a Fast-Growing EdTech Startup
Work directly with our founding team across marketing, customer success, and product development. Ideal for building a career in operations, marketing, or tech startups.
What You'll Do:
- Social media management & content creation
- Expert & client onboarding support
- Platform & development collaboration
- Direct mentorship from Harvard MBA founder
Flexible Schedule
Remote Work
Mentorship
Learning Opportunities
Key Responsibilities
Social Media Management
- Create engaging content for LinkedIn, Instagram, Twitter/X
- Develop and maintain a content calendar
- Schedule and publish posts using management tools
- Monitor engagement metrics and optimize strategy
- Engage with followers and build community
Expert & Client Onboarding Support
- Support onboarding for new experts and B2B clients
- Assist with profile creation and verification
- Coordinate onboarding sessions
- Create onboarding materials and user guides
Platform & Development Support
- Collaborate with development team on initiatives
- Assist with user acceptance testing (UAT)
- Document bugs and feature requests
- Contribute to product documentation
Qualifications
Required:
- Currently enrolled in or recently graduated from bachelor's program
- Strong written and verbal communication skills
- Experience with social media platforms
- Proficiency in Google Workspace or Microsoft Office
- Self-motivated, able to work independently
- Availability for 15-20 hours per week
Preferred:
- Experience with social media management tools
- Basic graphic design skills (Canva, Adobe)
- Familiarity with project management tools
- Interest in EdTech or career services
What You'll Learn
- Develop a portfolio of social media content with measurable results
- Gain experience in customer onboarding and UX optimization
- Learn to collaborate with technical teams
- Build professional relationships in the EdTech ecosystem
- Understand startup operations and growth strategies
Ready to Apply?
Send the following to careers@winning.careers:
- Your resume
- Brief cover letter explaining your interest
- Links to social media accounts you've managed
- One example of content you'd create for Winning.Careers
Applications reviewed on a rolling basis. Early applicants receive priority.
Full-Time • Remote
Sales Director
Be Our First Sales Hire. Build Something Extraordinary.
Lead B2B sales efforts targeting higher education institutions. Build the sales function from scratch and define our go-to-market strategy.
What You'll Do:
- Own the entire B2B sales cycle
- Target 3,000+ institutions in Year 1
- $54K-$210K+ earning potential
- 0.5%-1.5% equity grant
Equity Grant
Uncapped Commission
Expense Account
Leadership Path
Key Responsibilities
- Own the entire B2B sales cycle from prospecting to close
- Build a pipeline of university and private school clients
- Develop and execute a territory plan targeting 3,000+ institutions in Year 1
- Build relationships with C-level executives, Deans of Career Services, and VP-level decision-makers
- Conduct compelling product demonstrations and articulate ROI
- Negotiate contracts and navigate complex institutional buying processes
- Collaborate with CEO to refine messaging and sales strategy
- Document learnings and develop repeatable sales playbooks
- Represent Winning.Careers at industry conferences
Qualifications
Required:
- 5+ years of B2B sales experience (EdTech, SaaS, or higher education)
- Proven track record of closing six-figure annual contract values
- Experience selling to higher education institutions
- Self-starter mentality for 100% commission environment
- Excellent communication, presentation, and negotiation skills
Preferred:
- Experience selling PeopleGrove, Handshake, Symplicity, or similar platforms
- Existing relationships within university career services
- Understanding of higher education technology landscape
- Startup experience and comfort with ambiguity
Commission Structure
| Product Tier | Annual Value | New Deal | Renewal |
|---|---|---|---|
| Tier I - Core | $10,000 | 25% ($2,500) | 10% ($1,000) |
| Tier II - Professional | $15,000 | 30% ($4,500) | 12% ($1,800) |
| Tier III - Honors | $20,000 | 30% ($6,000) | 15% ($3,000) |
| Tier IV - Summit | $40,000 | 30% ($12,000) | 15% ($6,000) |
Earning Potential
Conservative:12 Tier II deals = $54,000
Target:20 Tier III deals = $120,000
Top Performer:30 Tier III + 10 renewals = $210,000+
Additional Benefits
- Equity Grant: 0.5% - 1.5% fully diluted (4-year vest, 1-year cliff)
- Accelerators: 35% commission after exceeding annual quota
- Spiff Bonuses: $2,500 first deal; $5,000 quarterly targets
- Expense Account: Monthly budget for travel and conferences
Ready to Apply?
Send your resume and a brief note on why you're excited about this opportunity to careers@winning.careers.
We particularly encourage candidates with PeopleGrove or EdTech sales experience to apply. Tell us about your biggest win in higher education sales!
Why Join Winning.Careers?
Be part of something extraordinary
Ground-Floor Opportunity
Join at a pivotal growth stage. Your contributions will directly impact our success as we scale from pilots to nationwide deployment.
Meaningful Impact
Help students and young professionals access the mentorship they need to succeed. Make a real difference in people's lives.
Experienced Leadership
Learn from our founder (Harvard MBA, $2.1B+ revenue generated) and Board members from Meta, McKinsey, BCG.
Career Acceleration
Develop transferable skills in a high-growth environment. Build a track record of impact that opens doors to leadership opportunities.
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Target Institutions
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Market Opportunity
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APIs Powering Platform
Ready to Shape Your Future?
We're reviewing applications on a rolling basis. Early applicants receive priority consideration.
Questions? Email us at careers@winning.careers