Head of Sales

About Peppy

Peppy is transforming access to specialist healthcare through employer benefits. We partner with leading organisations to provide employees with expert support across menopause, fertility, pregnancy, men’s health and women’s health. Our services combine clinical expertise with technology to deliver meaningful, accessible care to employees around the world.

Peppy works with enterprise organisations and global employers, including Fortune 500 companies, partnering with HR, People and Benefits leaders to deliver specialist healthcare support at scale.

We are a Series B company at an exciting stage of growth, with strong demand for our services and significant opportunity to scale internationally.

As we continue to grow our commercial organisation, we are hiring a Head of Sales to report to our SVP Growth and to lead our new business function and help scale our enterprise revenue engine.

The Role

We are looking for an experienced Head of Sales to lead and develop Peppy’s new business sales team as we enter the next stage of growth.

You will be responsible for driving sales performance across the team, strengthening our enterprise sales capabilities, and building the operational foundations required to scale a high-performing commercial organisation.

Peppy sells to HR, People and Benefits leaders in large enterprise organisations, often navigating complex buying groups and multi-stakeholder decision processes. Success in this role requires a leader who understands enterprise B2B sales deeply and can develop teams to consistently win complex deals.

Sales cycles typically involve multiple stakeholders across HR, benefits, procurement and senior leadership, requiring strong consultative and value-based selling.

You will work closely with the SVP Growth and broader leadership team to refine our sales strategy, improve execution across the funnel, and build a world-class commercial team.

Team Structure

You will lead a growing new business team consisting of: SDRs & AEs. You will be responsible for the performance, development and scaling of this team.

Key Responsibilities

Revenue Leadership

• Own revenue performance across the new business sales team.
• Ensure strong pipeline coverage and predictable forecasting.
• Improve conversion rates and sales cycle efficiency.
• Support the team in progressing and closing complex enterprise opportunities.
• Own sales forecasting, pipeline health and performance metrics across the new business organisation.

Sales Excellence & Coaching

• Develop the team’s capabilities in enterprise sales best practice, including value-based selling, stakeholder management and objection handling.
• Run structured pipeline reviews, deal reviews and win/loss analysis.
• Establish consistent sales standards and expectations across the team

Sales Operations & Process

• Build scalable sales processes and operating rhythms.
• Improve forecasting discipline and pipeline visibility.
• Ensure strong CRM hygiene and reporting.
• Partner with Growth, Marketing and RevOps to optimise lead generation and conversion

Sales Strategy

• Refine and strengthen Peppy’s enterprise sales motion.
• Provide market insights and feedback to leadership.
• Help shape messaging and positioning for HR and benefits buyers.
• Partner with Product, Marketing and Customer teams to ensure market feedback and customer insights inform product development and go to market strategy.

Team Development

• Recruit, onboard and develop high-performing sales talent.
• Establish clear performance expectations and development pathways.
• Build a culture of accountability, coaching and continuous improvement.
• Explore and implement AI tools and automation to increase team productivity, enhance prospecting and sales insights, and scale the effectiveness of the sales organisation.
• Lead hiring for future sales roles as the team scales, ensuring we attract and retain exceptional commercial talent.

What Success Looks Like in This Role

• Consistent achievement of new business revenue targets
• Strong pipeline coverage and improved forecast accuracy
• Increased win rates across enterprise opportunities
• A highly capable sales team executing consistently strong enterprise sales practices
• Scalable sales processes that support Peppy’s continued growth

What We’re Looking For

Experience

• We are looking for a sales leader who combines strong commercial experience with the ability to build and develop high performing teams.
• Experience leading Account Executives and SDR teams.
• Experience as a Head of Sales or senior sales leader within a high-growth company.
• Strong background in enterprise B2B sales earlier in your career, with experience closing complex deals.
• Experience operating in a scaling SaaS or technology business.
• Track record of improving sales performance through coaching, structure and operational discipline.

Skills

• Strong enterprise sales understanding.
• Excellent coaching and leadership capability.
• Structured and data-driven approach to sales performance.
• Strong operational discipline and forecasting capability.
• Ability to operate effectively in a fast-growing environment.

Leadership Style

• Ambitious and works collaboratively with other departments- from marketing, to finance and legal - to deliver results.
• Hands-on and highly engaged with team development.
• Analytical and operationally strong.
• Comfortable navigating ambiguity in scaling companies.
• Motivated by building and developing high-performing teams.

Much like us, we know you’re into perks and benefits, so here’s a list of ours:

• Access to Peppy: You can receive free unlimited access to the Peppy app to use our Menopause, Fertility, Baby, Women’s Health or Men’s Health services
• Health & Wellbeing: You will receive Private Medical Insurance through Vitality, including VitalityGP, optical, dental and hearing coverage
• Financial Wellness: You have access to your own confidential financial wellbeing coach and resources, through Bippit
• Parental Leave: We have a generous Enhanced Family Leave policy, whether you or your partner are giving birth, going through surrogacy or adoption
• Pension: We offer an up to 5% employer pension contribution scheme through Cushon
• Holidays: Peppy employees in the UK get 25 days holiday per year, plus bank holidays
• Hybrid: 2 or 3 days a week in-person with our Growth team in London would be amazing, but we're flexible to individual circumstances.
• Socials: We encourage our employees to join our in-person team events and socials to build stronger connections within your team. If you live outside London, your travel expenses for these events are on us too!
• Tech: New joiners receive a company MacBook delivered in time for your first day

Equality & Diversity:

Peppy's mission is to help people in life's most challenging journeys. We pride ourselves on being an equal opportunity employer, committed to equality and diversity amongst both our employees and prospective applicants. We ensure that all applicants are treated equally and fairly throughout our recruitment process.