Head of Sales

Head of Sales

Full-Time No working from home possible
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At a Glance

  • Tasks: Lead the UK sales team and drive enterprise deals in AI adoption.
  • Company: Join PAIR, a fast-growing AI adoption platform with a strong revenue trajectory.
  • Benefits: Competitive salary, stock options, and a dynamic work environment.
  • Other info: Be part of a diverse team focused on innovation and growth.
  • Why this job: Shape the future of AI in enterprises and make a real impact.
  • Qualifications: Proven track record in enterprise sales and team leadership.

Carlos Espinal, Managing Partner at Seedcamp, pointed to PAIR's revenue traction as some of the strongest he sees across most early stage portfolios. Our ARR went up 1,400% in 2025, has grown by around 100% again YTD, and is on track to reach more than 5x by year end. To continue on this trajectory, we are looking for a UK Head of Sales! PAIR is the layer between AI tool deployment and measurable business outcomes. We are defining a new category with our AI adoption platform which helps Enterprises navigate the challenges of AI today and helps them anticipate the ones for tomorrow.

You will own the UK sales engine and lead the team that gets us there. We are a 33-person company (hiring rapidly) with 7-figure ARR and our customers already include organisations such as PwC, the Ministry of Justice, healf, and The Crown Estate. The new Head of Sales will come in and turn strong selling into a repeatable motion, and who lands the deals that shape our Series A and beyond.

What you'd own:

  • The number: Carry and deliver the UK sales target. Own the forecast, the coverage and the conversion, and hold the team to it.
  • The motion: Turn a founder-led sale into a process the team can run without you: discovery, multi-threading, mutual action plans and stage discipline that hold up under pressure.
  • The team: Raise the enterprise game of a strong group of Account Executives through 1-1s, deal reviews and forecasting. Set a high bar and hold it through shared commitment to what we are building here.
  • The strategic deals: You will actively be involved in the important deals yourself and support AEs in senior rooms.
  • The story and the price: Keep our positioning and pricing logic intact as the team scales.
  • The growth of the team: Hire, onboard and ramp new Account Executives as we scale through 2026 and beyond.

The sale:

These are enterprise deals: aiming for six and seven figures, 3-9 months sales cycle, multi-stakeholder and multi-threaded, and most often direct (not through tenders). The conversation opens on AI, where the customer is, what they have tried, what has not stuck, and moves to the key organisational problem: embedding new capability into how thousands of people work. PAIR is how that becomes measurable, operational and durable.

The deliberate shift this year is moving from pilots that scale towards larger initial lands, where PAIR becomes one of the top priorities a customer will put budget behind. Your team earns the right to advise the C-suite, IT and Security, HR and L&D, and procurement, often in the same week.

About you:

You have built an enterprise sales motion yourself and you know what it takes to make excellence repeatable and scalable. You have carried and hit a number as a seller, and you have managed and developed sellers. You lead from the front. You are in the detail and diligent, you work hard, and you bring urgency and ownership to everything you do. You have a growth mindset and a real appetite to learn. You are curious about AI adoption as an organisational problem, and you can hold a credible, senior conversation about it. You communicate clearly at executive level: concise on the page, confident in the room.

Must-have experience:

  • A track record of selling enterprise software or AI into large organisations, including deals of GBP 1M+, through long, complex, multi-threaded cycles, won by selling direct rather than through tenders alone.
  • Evidence of having built or materially shaped a sales motion: playbook, qualification, process and forecast rigour.
  • Experience managing and developing quota-carrying Account Executives.
  • Strong commercial acumen: proposals, statements of work, pricing and negotiation.
  • Affinity for technology and AI.
  • London-based, in the office 3-5 days a week.

Nice to have:

  • Early-stage or start-up experience.
  • Sold something without the cover of an established brand: a new category, an unproven product, or a company the buyer had never heard of.
  • Experience selling a technical product.
  • Exposure to workforce transformation, change management or adoption programmes.
  • Existing enterprise black book.

The team, and how we work:

This is a team that works hard and holds a high bar. The opportunity is unusually large: you would be building at the front of a real shift in how organisations work, with the growth and impact that come with that. In return we expect ownership, pace and accountability. We give high trust and clear outcomes.

We are also expanding into the US, where we are building a team on a steep trajectory. This role is UK-focused: your mandate is to build and lead the UK engine but you would be joining a company scaling on two fronts and moving quickly on both.

Compensation & Process:

  • Location: London (3-5 days in the office)
  • Start date: As soon as possible
  • Reports to: Commercial Director
  • Compensation: £195k-£214k OTE, plus stock options on a 60/40 base-to-variable split

Head of Sales employer: PAIR

PAIR is an exceptional employer that fosters a dynamic and innovative work culture, perfect for those passionate about AI and its transformative potential. With a focus on employee growth and development, team members benefit from competitive compensation packages, including stock options, and the opportunity to work closely with ambitious organisations across the UK. Located in London, our team enjoys a vibrant city atmosphere while engaging in meaningful projects that drive real business outcomes.

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Contact Details:

PAIR Recruitment Team

StudySmarter Expert Advice🤫

We think this is how you could land Head of Sales

Leverage Your Network

In sales and business development, who you know can often be as important as what you know. Get involved with local networking events or industry meetups to connect with key players. Don't be shy—share your passion for the field and let folks know you're on the lookout for opportunities!

Show Your Skills Through Real-World Results

When targeting a full-time role like Head of Sales at PAIR, presenting tangible results from your previous sales experience can set you apart. Bring along case studies or examples of how you've closed deals or expanded accounts, and don't forget to showcase your problem-solving prowess. It’s all about quantifying your success!

Engage with Sales Communities

Dive deep into online sales communities, like Sales Hacker or LinkedIn groups dedicated to sales professionals. Engaging in discussions and sharing insights can boost your visibility and might just put you on the radar of hiring managers looking for fresh talent in business development.

Direct Applications Matter

While we all know the online application route, consider sending direct applications to companies you admire, including PAIR. Tailor your message to explain why you’re drawn to them and how you can contribute as a Head of Sales. Sometimes, a personal touch can grab attention faster than a generic application!

We think you need these skills to ace Head of Sales

Enterprise Sales
Sales Strategy Development
Account Management
Forecasting
Negotiation Skills
Team Leadership
Process Improvement

Some tips for your application 🫡

Show Off Those Sales Skills:In your CV and cover letter, highlight any previous sales or business development experience you have. Use numbers and examples to showcase your achievements – did you exceed sales targets or bring in new clients? Make those accomplishments shine!

Tailor Your Message for PAIR:When writing your cover letter, make sure to tailor your message specifically for PAIR. Show that you know the company’s mission and how your skills align with their goals in the sales landscape. This personalised touch will grab their attention!

Keep It Professional Yet Engaging:Sales is all about relationships, so while you want to maintain professionalism in your application, don’t be afraid to let your personality shine through. Engage the reader and demonstrate your enthusiastic approach to sales and business development!

Proof of Performance:Include any relevant certifications or training you’ve undertaken in sales or negotiation tactics. If you’ve attended workshops or courses, list these to showcase your commitment to professional development. This extra touch can set you apart from the competition!

How to prepare for a job interview at PAIR

Know Your Sales Methodologies

Brush up on popular sales methodologies like SPIN Selling or Challenger Sales. Being able to discuss these techniques and how you've applied them will show PAIR that you understand the role and can hit the ground running in the sales game.

Demonstrate Your Deal-Making Skills

Prepare to share stories from your past experiences where you closed deals, overcame objections, or started new client relationships. We want to show PAIR that you’re not just about numbers but also about building lasting connections in business development.

Prepare for Role-Play Scenarios

In a full-time sales interview, don’t be surprised if they throw in a role-play exercise to test your pitching skills. Practising how you would pitch a product or handle an objection will help us shine in this simulation—think of it like a dress rehearsal for your future sales calls!

Align Your Goals with the Company’s Vision

Take a moment to reflect on how your career ambitions align with PAIR’s objectives. When we articulate how our personal growth ties in with the company’s goals, it shows commitment and a genuine interest in contributing to their success.