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
We are looking for a commercially driven Head of New Business to lead new business growth. This is a senior,
hands-on role combining individual quota ownership with responsibility for building, leading, and developing a highperforming
sales team.
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 TiPJAR
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 deal deep dives
- 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
If you're looking to join a small but mighty team on a mission to change the world of tipping and reward teams fairly – we’d love to hear from you.
Apply now and help us shape the future of fair tipping.
Interview Process
We keep our process simple, transparent, and human. You’ll meet the people you’ll actually work with, and we’ll give you space to show how you think, communicate, and collaborate.
- Initial Conversation (20–30 mins) - A relaxed call to learn more about you, your experience, and what you’re
looking for. - Hiring Manager Competency Interview (45 mins) - A deeper conversation about the role, your skills, and how
you approach your work. - Task Exercise - A 60 minute, role-relevant task that gives you a feel for the work and helps us understand your thinking.
- Final Conversation - A conversation with a Director or CoFounder, giving you the chance to ask questions and
get a real sense of what it’s like to work here.
We move quickly and communicate openly throughout. No surprises, no long waits, no unnecessary steps
Preemployment Screening
All offers of employment at TiPJAR are subject to preemployment checks. This includes a DBS check, employment referencing, and confirmation of your right to work. Employment can only begin once you have demonstrated your legal right to work in the UK, in line with the Immigration, Asylum and Nationality Act 2006.
Equal Opportunities
TiPJAR is an equal opportunities employer. We welcome applications from everyone, regardless of age, disability, gender identity or expression, marital or civil partnership status, pregnancy or maternity, race, religion or belief,sex, or sexual orientation. We are committed to building an inclusive workplace where everyone feels valued and able to thrive.
Please note, that due to the high volume of applications received, we regret to inform you that we are unable to provide detailed feedback to candidates who have not been shortlisted (for further consideration).