Head of Sales, Rebrandly

• You'll thrive in an environment where you can directly impact revenue through your own sales efforts
• 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
• 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
• API/Developer Tools Experience: Understanding of how technical teams evaluate and adopt developer-focused products

Desirable

• 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 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
• 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
• 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