Head of SMB and Commercial Sales

Superhuman offers a dynamic hybrid model, and candidates in this role can be based remotely. You may be expected to travel to meet in person during your team’s scheduled collaboration weeks. Managers will determine in-person time according to business needs.

This hybrid approach helps foster trust, innovation, and a strong team culture, with the flexibility of working from home whenever you need focus time.

Grammarly is now part of Superhuman, the AI productivity platform on a mission to unlock the superhuman potential in everyone. The Superhuman suite of apps and agents brings AI wherever people work, integrating with over 1 million applications and websites. The company’s products include Grammarly’s writing assistance, Superhuman Docs' collaborative workspaces, Mail’s inbox management, and Go, the proactive AI assistant that understands context and delivers help automatically. Founded in 2009, Superhuman empowers over 40 million people, 50,000 organizations, and 3,000 educational institutions worldwide to eliminate busywork and focus on what matters. Learn more at superhuman.com and about our values here.

Superhuman’s go-to-market teams are shaping the future of workplace communication. As a member of our team, you will be crucial in expanding the use of our innovative, trustworthy AI writing tools. We strive to ensure that every organization can communicate effectively and efficiently. If you are passionate about transforming the way professionals connect and collaborate, we would love to hear from you.

As Head of SMB and Commercial Sales, you will lead the heritage Grammarly and Superhuman Go teams within Superhuman’s commercial BU structure, owning the strategy, team development, and revenue performance of the Go sales motion across SMB and Mid-Market segments. You will operate as the senior sales leader for the business unit, working within the ATU/STU model and partnering closely with Superhuman’s broader commercial leadership to drive pipeline, bookings, and customer expansion.
This is a people-first leadership role for a seasoned commercial leader who can inspire and develop a team of sellers, build scalable GTM processes, and elevate the team’s capability to operate at the highest levels of enterprise selling, including C-suite engagement, multi-stakeholder deal navigation, and solution-based discovery for a multi-faceted product. In this role, you will:

• Lead, coach, and develop a team of front-line managers and AEs to consistently exceed revenue and activity targets across all segments

• Own the Go SMB and Commercial sales strategy and GTM execution, partnering with ATU leadership, Product, CS, and Marketing to drive a cohesive, high-performance sales motion

• Build and maintain a team culture grounded in accountability, psychological safety, and continuous improvement, where sellers feel supported, and their work has clear impact

• Drive rigorous pipeline management and forecasting discipline, maintaining accuracy and visibility for senior leadership

• Define and standardize onboarding, sales methodology, and enablement to reduce ramp time and improve consistency

• Champion enablement: identify skill gaps, partner with the enablement function, and ensure the team has the tools, training, and frameworks to run complex, multi-value-prop deals

• Serve as the senior commercial presence on key deals, guiding team strategy, supporting C-suite conversations, and helping navigate late-stage complexity

• Partner cross-functionally with Product, Marketing, and CS leadership to shape the product narrative, surface customer insights, and influence roadmap priorities

• Represent the Go sales team in BU leadership discussions, providing a grounded sales perspective on go-to-market decisions

• Hire, onboard, and retain exceptional talent, building a bench ahead of growth and planned leave coverage

• 10+ years of SaaS sales experience, with at least 5 years in a sales leadership role managing a team of Account Executives

• Proven track record of building and leading high-performing enterprise sales teams in a land-and-expand or expansion-driven motion

• Experience leading in a matrixed or multi-product selling environment (e.g., STU/ATU, overlay, or specialist AE model) — comfortable driving results without direct control of all inputs

• Deep expertise in enterprise sales cycles with demonstrated success engaging VP and C-Suite stakeholders across IT, procurement, and multiple lines of business

• Background in collaboration, productivity, or work management SaaS tools strongly preferred; experience at a progressive tech company with a strong product culture is a plus

• Strong coaching orientation — known for developing sellers, not just managing pipeline; can identify skill gaps and build targeted development plans

• Excellent command of a recognized sales methodology (e.g., MEDDIC, MEDPICC, Challenger, or equivalent) and ability to embed it into team practice

• Skilled at building systems and processes in ambiguous environments — can design onboarding, enablement frameworks, and repeatable playbooks

• Data-driven approach to pipeline management and team performance; Salesforce proficiency required

• Exceptional cross-functional partnership skills — able to align with Product, CS, Marketing, and executive stakeholders with credibility and influence

• Fluent in using AI tools in daily workflows and able to model and champion AI-enabled ways of working across the sales team.

• Has a demonstrated ability to work independently with minimal guidance, proactively manages tasks and priorities across multiple projects, analyzes and executes work efficiently, collaborates effectively with cross-functional teams, and thrives in fast-paced, results-driven environments.

Superhuman offers all team members competitive pay along with a benefits package encompassing the following and more:

• Excellent health care (including a wide range of medical, dental, vision, mental health, and fertility benefits)

• Disability and life insurance options

• 401(k) and RRSP matching

• Paid parental leave

• 20 days of paid time off per year, 12 days of paid holidays per year, two floating holidays per year, and flexible sick time

• Generous stipends (including those for caregiving, pet care, wellness, your home office, and more)

• Annual professional development budget and opportunities

Superhuman takes a market-based approach to compensation, so base pay may vary by location. Our US locations are categorized into two compensation zones based on proximity to our hub locations.

Base pay may vary considerably depending on job-related knowledge, skills, and experience. The expected salary ranges for this position are outlined below by compensation zone and may be modified in the future. The expected “On Target Earnings” (OTE) for this role is outlined below and may be modified in the future.

Zone 1: $429k - $536k

Zone 2: $386k - $482k

The commission portion for this role will be 40% of the On-Target Earnings (OTE).

For more information about our compensation zones and locations where we currently support employment, please refer to this page. If a location of interest is not listed, please speak with a recruiter for additional information.

At Superhuman, we value our differences, and we encourage all to apply—especially those whose identities are traditionally underrepresented in tech organizations. We do not discriminate on the basis of race, religion, color, gender expression or identity, sexual orientation, ancestry, national origin, citizenship, age, marital status, veteran status, disability status, political belief, or any other characteristic protected by law. Superhuman is an equal opportunity employer and a participant in the US federal E-Verify program (US). We also abide by the Employment Equity Act (Canada).