Head of Sales

About GlossGenius GlossGenius is building an ecosystem enabling entrepreneurs to succeed. We empower small business owners to focus on being creators, not admins, by offering a range of business management tools including booking and scheduling, marketing, analytics, payment processing and much more. Over 100,000 small business owners have chosen to rely on GlossGenius every day to run their entire set of business operations. Joining its powerful, intuitive platform with its vibrant, distinguished brand, GlossGenius is the ideal combination of a fintech, SMB software, and consumer company all in one. About the Role As the Head of Sales, you will be the strategic leader responsible for scaling and optimizing GlossGenius's entire sales organization. Reporting directly to the Chief Revenue Officer, you will help architect and execute our go-to-market strategy across all sales channels—outbound, inbound, field—while building a high-performing team capable of achieving ambitious growth targets in the SMB market. This is a transformational leadership role requiring someone who has successfully scaled a sales organization from 30 to 100+ people and understands the operational rigor, process discipline, and cultural foundations necessary to sustain hypergrowth. You'll be responsible for the full sales function, including hiring and developing multiple layers of leadership (Sales Managers, Directors), establishing best-in-class sales processes, driving cross-functional alignment, and ensuring we're breaking into new customer segments while optimizing unit economics. You will report to the Chief Revenue Officer. You must be commutable to our NYC headquarters. We default to being in-office 3-4 days per week with required attendance on Tuesdays and Thursdays. What You'll Do Design and execute a comprehensive scaling plan to grow the sales team from 30 to 100+ team members while maintaining or improving productivity metrics Establish clear career progression frameworks and professional development programs that attract and retain top sales talent Architect and continuously optimize our multi-channel GTM strategy across inbound and outbound sales – including expansion into new verticals and segments In conjunction with Revenue Operations, own the sales methodology, playbooks, and enablement programs that drive consistent execution across all channels Build a data-driven culture with rigorous forecasting and accountability across key metrics: ramp time, quota attainment, win rates, ASP, and CAC payback Provide input into the design and management of compensation plans, quota allocation, and territory assignments that drive the right behaviors and outcomes Support the evaluation, implementation, and optimization of sales technology stack (CRM, sales engagement platforms, conversation intelligence, forecasting tools) leveraging AI and emerging tools to drive productivity What We're Looking For 10+ years of sales experience in B2B SaaS or SMB software, with at least 7 years in sales leadership roles Proven track record of scaling a sales organization from 30 to 100+ people while maintaining or improving efficiency metrics Demonstrated success in SMB sales with understanding of high-velocity sales motions and the unique challenges of serving small business customers Experience managing multiple layers of sales leadership (managers and directors) with a track record of developing leaders who go on to greater responsibility Strategic thinker who can balance long-term vision with short-term execution and knows when to prioritize each Ability to drive alignment across cross-functional stakeholders and influence without authority Experience implementing sales methodologies and building repeatable, scalable processes Deeply analytical with expertise in sales metrics, funnel optimization, and predictive forecasting Proficiency with modern sales technology stack including Salesforce or HubSpot (CRM), Outreach or Salesloft (engage ... (truncated, view full listing at source)