Head of Business Development

HELLO, WE’RE TIPJAR

TiPJAR exists to make appreciation fair, transparent, and direct and in joining our team, you’ll play a part in putting tipping back in the hands of the people who earn it and rely on it most.

What began as a bold idea has become a global platform changing the daily lives of thousands. We’re doing something no one has done before, and that means we move fast, challenge assumptions, and push through walls that would stop most teams.

We’re a values-led, people-first company. We celebrate wins loudly, communicate openly, innovate boldly, and believe success is something we build and share together.

The role

You will report directly to the Chief Commercial Officer and play a critical role in shaping TiPJAR’s go-to-market strategy, sales execution, and revenue predictability.

What You’ll Be Doing Day to Day:

New Business and Revenue Delivery

• Own personal new business quota while being accountable for overall team performance
• Generate consistent outbound activity every week across:
• Cold and warm prospecting via phone, email, and LinkedIn
• Attending networking and industry events
• Creating and engaging with social media content
• Identify, qualify, and close opportunities within our ICP, including group operators, multi-site brands, and strategic partners
• Navigate complex, multi-stakeholder enterprise sales cycles and regulatory landscapes including tronc legislation, NI mitigation, and HMRC guidance
• Lead high-value enterprise negotiations including pricing, commercials, and contract structuring
• Build strong senior stakeholder relationships and clearly articulate the commercial and operational value of

Sales Leadership and Team Development

• Build, hire, onboard, and develop a high-performing sales team as the business scales
• Act as day-to-day leader for the sales function, coaching on pipeline management, deal strategy, and execution
• Set clear expectations for activity levels, conversion metrics, and performance standards
• Conduct regular pipeline reviews, forecasting sessions, and deep dives into deals
• Create a culture of accountability, continuous improvement, and commercial excellence

Sales Process, Strategy, and Operations

• Continuously refine TiPJAR’s sales methodology, qualification framework, and enterprise sales playbooks
• Own pipeline forecasting, CRM accuracy, and reporting to ensure predictability and confidence
• Establish and monitor sales KPIs, dashboards, and performance metrics
• Contribute to territory design, account segmentation, and target account planning aligned to ARR goals
• Partner closely with Marketing to shape lead generation strategy, messaging, and campaign effectiveness
• Work cross-functionally with Product and Customer Success to deliver tailored solutions and ensure strong handovers
• Feed structured market insight, customer feedback, and win-loss analysis back into the wider business

WHAT WE’RE LOOKING FOR

• 5+ years in B2B saas sales, ideally in hospitality tech
• Experience in enterprise sales or complex multi-site deals with longer sales cycles
• Understanding of regulatory frameworks – experience navigating financial compliance or employment/tax legislation is a strong plus
• Exceptional written, verbal and presentation skills
• Hunter mentality – resilient, disciplined and able to self-generate leads
• Comfortable owning outbound KPIs (calls, emails, demos, follow-ups) week-in, week-out
• Curious, consultative and able to understand customer pain points and tailor solutions accordingly
• Thrives in a fast-paced scale-up and is excited to help shape our future

WHAT YOU’LL GET IN RETURN

• Flexible working hours and hybrid working
• Competitive salary, commission, bonus and benefits
• 33 days holiday (including bank holidays)
• Company laptop or mac
• Company mobile phone
• Rewards scheme with discounts across retail, hospitality, services and much more
• Expenses covered for travel/events
• The opportunity to work from anywhere – including up to 4 weeks abroad each year
• Career progression in a rapidly growing business
• Access to some of the UK’s best hospitality operators
• Regular social events