Head of Sales

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.

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 and understands the operational rigor, process discipline, and cultural foundations necessary to sustain hyper-growth. 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.

• →Design and execute a comprehensive scaling plan to grow the sales team while 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
• →Evaluate, implement, and optimize the sales technology stack — with a particular emphasis on AI-powered tools across prospecting, conversation intelligence, forecasting, and rep coaching — and build a culture where the team uses AI to sell smarter, not just faster

• 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 while improving productivity 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 (engagement), Gong or Chorus (conversation intelligence)
• A demonstrated point of view on how AI is reshaping high-velocity SMB sales — you've already integrated AI into your team's motion in a meaningful way, whether through automated prospecting, AI-assisted coaching, predictive forecasting, or rep enablement, and you know how to drive adoption across a large team without losing the human elements that close deals
• Comfort evaluating and making buy vs. build decisions on AI sales tooling, and the credibility to bring skeptical sellers along on the journey
• Process-oriented with experience designing and implementing scalable systems and workflows