Director of Sales / Founding Sales Leader — Global AI-Native Tech Talent Venture

Director of Sales / Founding Sales Leader
We're looking for an exceptional Director of Sales / Founding Sales Leader to lead the commercial growth of SkillsCapital's new AI Career Intelligence vertical.
This is an opportunity to join at the beginning of a potentially category-defining AI-native Career Intelligence business, while leveraging the technology, intelligence, and AI capabilities SkillsCapital has already built.
This is not a traditional sales management role.
This is a builder's role.
You'll work directly with the founders and leadership team to define the market, build the customer acquisition engine, establish the sales playbook, drive early revenue, and progressively build the sales organization around this new vertical.
For the right person, this role can evolve into VP Sales and ultimately Chief Sales Officer for the Career Intelligence business, with significant ownership of its global commercial strategy and growth.
About SkillsCapital
SkillsCapital is an AI-native Talent Intelligence platform helping organizations discover, evaluate, and deploy specialized technology talent across enterprise technology ecosystems.
Our existing technology foundation includes:
AI-Native Talent Intelligence
AI-Native Talent Engine
Agentic AI
Intelligent matching and evaluation
Semantic intelligence
Workflow automation
Talent data and intelligence
Expert-led validation
Deployment-readiness intelligence
These capabilities are already operational, production-ready, and deployed in real business workflows.
We have:
Built and launched a production-ready AI-native Talent Intelligence platform
Built and deployed an AI-Native Talent Engine
Developed proprietary AI and Talent Intelligence capabilities
Built Agentic AI-driven end-to-end workflows
Established customer relationships across the United States, United Kingdom, Europe, Australia, and the Middle East
Achieved a multi-million-dollar annual run rate
Bootstrapped the business to profitability without external funding
The Opportunity: AI Career Intelligence
SkillsCapital is now extending its AI and Talent Intelligence foundation into a new B2C Career Intelligence vertical.
We see an opportunity to build a fundamentally more intelligent platform for technology professionals—helping them navigate their careers using AI, professional intelligence, market intelligence, personalized recommendations, and intelligent workflows.
The product is being built on:
Talent Intelligence + AI-Native Talent Engine + Agentic AI + Matching + Evaluation + Technology Intelligence
This creates a significant opportunity at the intersection of:
AI × CareerTech × Talent Intelligence × Future of Work
The Director of Sales will be responsible for turning this product opportunity into a scalable global business.
What You'll Own
1. Build the Revenue Engine
Own early revenue generation.
You'll personally identify prospects, engage customers, conduct sales conversations, demonstrate the product, handle objections, close customers, and build relationships.
2. Define the Sales Strategy
Work with the founders to determine:
Who should we sell to first?
Which customer segments have the strongest pain?
What should our initial offer be?
What pricing model works?
Which channels should we prioritize?
What makes customers convert?
What drives retention and expansion?
You'll help turn these answers into a repeatable GTM model.
3. Build Customer Acquisition
Develop acquisition strategies across:
Direct outreach
Communities
Partnerships
Referrals
Content-led acquisition
Social channels
Product-led growth
Events
Professional networks
4. Own Consultative Selling
Understand the professional's career challenges and connect them to the Career Intelligence product.
You'll need to sell outcomes and intelligence, not simply product features.
5. Build the Sales Playbook
Develop repeatable processes for:
Prospecting → Discovery → Product Demo → Qualification → Conversion → Onboarding → Retention → Expansion
Document what works and turn it into a scalable sales system.
6. Drive Product-Led Sales
Work closely with product and technology teams to understand:
Product usage
Activation
Conversion
User engagement
Drop-off points
Customer feedback
Product-market fit
Use these insights to improve both the product and the sales journey.
7. Build Partnerships
Identify and develop partnerships with:
Professional communities
Technology associations
Training organizations
Certification ecosystems
Universities
Career platforms
Technology companies
Influencers and creators
Professional networks
8. Build the Sales Organization
Initially, this will be a hands-on builder role.
You'll personally drive the early sales motion.
As the business scales, you'll recruit and lead the sales organization, establish territories and processes, develop sales managers, and build the broader commercial function.
9. Build Sales Intelligence
Use AI and data to understand:
Customer acquisition
Conversion rates
Sales velocity
Customer segments
Buying behavior
Objections
Pricing
Churn
Expansion opportunities
10. Work Directly With Founders
You'll contribute to:
GTM strategy
Pricing
Product positioning
Customer segmentation
Partnerships
Market expansion
Revenue strategy
Product-market-fit decisions
What We're Looking For
We care more about commercial capability, ownership, creativity, execution, and results than titles or years of experience.
You may be a great fit if you have:
Proven sales experience in B2C technology, SaaS, AI, CareerTech, HRTech, EdTech, or professional platforms
Strong consultative selling ability
Experience selling technology products
Ability to build pipelines from scratch
Strong discovery and objection-handling skills
Excellent communication and storytelling
Strong customer empathy
Entrepreneurial mindset
Comfort with ambiguity
Ability to work directly with founders
Willingness to personally sell before building a team
Particularly valuable experience includes:
Consumer AI
Generative AI
CareerTech
HRTech
EdTech
Professional networks
SaaS
Marketplaces
Subscription products
Community-led businesses
Product-led growth
What We Value
We're looking for someone who thinks:
Customer before channel.
Value before features.
Revenue before activity.
Experimentation before assumptions.
Ownership before hierarchy.
You should be comfortable moving between:
Strategy → Prospecting → Discovery → Demo → Conversion → Customer Feedback → Growth
without needing a large team around you.
You should also be excited about using AI to transform the sales function itself.
The AI-Native Sales Opportunity
You'll have the opportunity to leverage AI across:
Prospect intelligence
Customer research
Personalized outreach
Sales preparation
Conversation intelligence
Follow-up
Lead qualification
CRM automation
Conversion analysis
Customer segmentation
Sales forecasting
Retention and expansion
The goal is to build a high-output commercial organization, not simply a large sales team.
Why This Opportunity
Build the sales engine for a new AI Career Intelligence category
Work on top of an operational AI technology foundation
Leverage SkillsCapital's AI-Na

Work arrangement
Yes