Head Of Sales - Remote Eligible

Sales Leader Opportunity At Rebrandly

Imagine building the go-to-market strategy for a martech SaaS platform that processes 3 billion user interactions (clicks) per month and powers the digital presence of brands like MetLife, NBA, Volvo, Zillow, and Versace. That's the opportunity waiting for you at Rebrandly, the world's most trusted link management platform.

We've steadily built something remarkable: a profitable, stable SaaS business serving 1.3 million users globally while maintaining an industry-leading 99.99% platform uptime SLA. Our 100,000 developers rely on our API daily, and we've achieved a 39% increase in customer clicks year-over-year – clear evidence of our strong product-market fit. Backed by Five Elms Capital and operating seamlessly across the US and EU regions, we have the financial foundation and strategic support to scale aggressively.

What sets us apart in our market category isn't just our scale – it's our technical sophistication. Our product features enterprise-grade compliance, including HIPAA and SOC 2 Type 2 certifications, collaboration features, superior domain management flexibility, and innovative security features that have become the differentiators helping us compete directly against market leaders and win.

The Opportunity

You'll join the leadership team as a direct report to the CEO, with meaningful input into strategic decisions around product roadmap, market positioning, and company direction. As we grow, this role naturally evolves into our VP of Sales position.

You'll be joining us at a pivotal inflection point as we evolve from our successful inbound-driven, PLG-heavy foundation into a systematic revenue generation engine. We're building an optimized PLG/SLG hybrid model that leverages our organic growth momentum while adding the strategic sales muscle needed to capture midmarket opportunities and accelerate our trajectory.

This is the ultimate player-coach opportunity where you'll carry quota while architecting our sales transformation. You'll roll up your sleeves to close deals and build relationships with midmarket and enterprise prospects, all while designing the scalable processes. You'll thrive in an environment where you can directly impact revenue through your own sales efforts.

You'll be selling to a diverse global customer base, including direct-to-consumer brands and service providers, digital marketing agencies, and technology platforms. Your prospects span multiple functional areas - marketing teams focused on campaign performance, product managers building integrated solutions, and customer success leaders optimizing user experiences. Success requires understanding varied buyer motivations across different industries, company sizes, and geographic markets.

What You'll Do

As a Player - Sales:

• You'll personally manage and close midmarket deals in the $30K-$100K+ range
• You'll execute outbound prospecting strategies to generate new pipeline, targeting marketing and technical decision-makers at B2C companies
• You'll gain and demonstrate deep product knowledge to address technical requirements while connecting features to business value
• You'll maintain a results-oriented mindset - you're not satisfied unless we're exceeding our sales targets

As a Coach - Sales Team Leadership:

• You'll build systematic outbound prospecting processes from scratch in partnership with Revenue Operations
• You'll track and communicate our sales performance KPIs, including trends in win rates, ACV, sale cycle times, and rep productivity, as well as conduct pipeline reviews to produce accurate sales forecasts.
• You'll optimize freemium-to-paid conversion via collaboration with Product, Growth, and RevOps
• You'll lead and manage the existing sales team on deal progression and closing techniques.
• You'll create repeatable sales processes and playbooks
• You'll motivate your team to go deep into the details about our product and other B2B SaaS products and services to better sell to customers

What We're Looking For

Essential Experience:

• 4-6 years of outbound quota-carrying sales experience at a SaaS B2B company, with at least 2 years of experience in mid-market
• 2-4 years of sales management/leadership experience
• Demonstrated success with PLG/Sales hybrid models and freemium conversions
• Experience building outbound motions from scratch with measurable results
• Track record of managing both individual quota and team development simultaneously
• Experience in personally selling to mid-market and technical buyers

Key Skills:

• Systematic prospecting and cadence development
• PLG/Product partnership and conversion funnel optimization
• Data-driven pipeline management and forecasting
• Cross-functional collaboration with Marketing, Product, Revenue Operations, and Customer Success
• Process building and sales methodology creation

Preferred Skills:

• API/Developer Tools Experience: Understanding of how technical teams evaluate and adopt developer-focused products
• Experience with marketplace sales (AWS, Azure, Google Cloud)
• Familiarity with the marketing technology landscape and popular tools
• Working understanding of product-led growth dynamics, account activation, and expansion strategies
• Experience selling to regulated industries (healthcare, finance, insurance) with compliance requirements

Why You'll Love Working at Rebrandly

Rebrandly provides its full-time US employees with comprehensive benefits, including:

• Health & Wellness: Comprehensive medical, dental, and vision coverage with generous company contributions toward monthly premiums to keep you and your family healthy. We cover 100% of the premiums for short-term and long-term disability, basic life and AD&D insurance. Plus additional support through HSA/FSA options and mental health resources with Talkspace.
• Work-Life Balance: Enjoy unlimited Flexible Time Off to recharge when you need it, giving you the flexibility to balance your professional and personal life.
• Financial Security: Build your future with our 401(k) plan featuring company matching, helping you invest in long-term financial well-being.
• Remote-First Culture: We're committed to supporting our distributed team with the flexibility and resources you need to do your best work from wherever you are.
• Our Values: Join a team that lives by our core values of Builder Mindset, Customer First, Transparency, and Gratitude. We believe in creating solutions, putting customers at the heart of everything we do, communicating openly, and appreciating the contributions of our teammates.

Rebrandly does not sponsor work authorization needs; candidates must have proper work authorization to work for any employer in the United States, without sponsorship from the company.

Rebrandly is an Equal Employment Opportunity and Affirmative Action Employer. Qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender perception or identity, national origin, age, marital status, protected veteran status, or disability status.