Principal Adviser – Sales

Our Principal Advisers work directly with founders, CEOs, and Boards of high-growth B2B media businesses to lead specialist scaleup programmes and build lasting value. The Principal Adviser – Sales brings deep commercial expertise to help clients build more predictable, scalable revenue — while also winning new business and shaping the firm's sales advisory product.

Collingwood is growing, and we are looking for a Principal Adviser – Sales to join our UK Advisory team. This is a permanent role with three equal dimensions: expert client delivery, leading new business from prospect to close, and building the sales advisory products that underpin our work. It is designed for someone who wants to do all three — not just one.

The role

You will lead sales-focused client engagements end-to-end: diagnosing commercial challenges, running workshops, and leaving clients with the tools and structures to build stronger, more scalable revenue. Sales strategy is the primary anchor, with the wider module suite spanning pitch and narrative development, customer journey optimisation, incentive scheme design, and rebooking strategy.

Alongside delivery, you will act as deal lead for new business — owning the full journey from prospect identification through to scoping, proposal, pitch, and signed engagement. You will bring your own network and use it. You will also take a hands‑on role in building and improving Collingwood’s sales advisory product: developing frameworks, playbooks, and templates that can be used consistently across the team, and working with the Chief Product Officer to productise the module suite.

Key responsibilities

• Lead sales strategy engagements: conducting sales team audits, assessing team structure and capability, developing strategic selling playbooks, and creating business cases for sales enablement investment.
• Deliver sales narrative and pitch development work, including building and refining master pitch decks and coaching client teams through live opportunities with key accounts.
• Map and optimise client buying journeys to increase conversion, improve retention, and grow customer lifetime value.
• Design and implement sales incentive and commission schemes aligned to the client’s strategic goals and growth plans.
• Develop rebooking strategies that transform rebooking from a reactive tactic into a scalable, year-round revenue programme.
• Develop high quality, insight-led client outputs, including sales audits, playbooks, frameworks, and implementation plans.
• Provide clients with clear, actionable recommendations grounded in their own data and commercial context, in line with the Collingwood Way.
• Work within the engagement structure set by the Strategic Adviser and Client Director, keeping the wider programme team aligned on sales workstream progress.
• Take “AI Audit” responsibility for all sales workstream deliverables, validating and enhancing Associate Adviser outputs against The Collingwood Way.
• Deliver other non-sales modules from the Collingwood product offering.

Business development and deal lead

• Own the full new business journey through scoping, proposal, pitch, and signed engagement.
• Build and actively work a pipeline of advisory prospects, targeting B2B media businesses within Collingwood’s ICP.
• Lead or co‑lead discovery meetings with prospective clients, diagnosing commercial challenges and positioning the right engagement scope.
• Write and present compelling proposals and pitches that articulate the value of Collingwood’s advisory work clearly and specifically.
• Maintain and grow a personal network across the B2B media sector, generating introductions and referrals that feed the firm’s pipeline.
• Attend industry events and engage consistently with prospects and referrers on social media.
• Identify upsell and cross‑sell opportunities within existing engagements; contribute to renewals and account expansion.
• Collaborate with the wider BD team on joint opportunities, sharing pipeline visibility and supporting colleagues’ deals where relevant.

Product build

• Take an active role in developing and improving Collingwood’s sales advisory product: building and refining frameworks, templates, playbooks, and module structures for use across the team.
• Work with the Chief Product Officer to productise sales modules — translating delivery experience and client insights into scalable, consistently excellent products.
• Identify gaps in the current sales module suite and propose new products based on unmet client needs or emerging market challenges.
• Document delivery best practice in a way that enables other advisers to deliver sales modules to a high standard, reducing reliance on individuals.
• Build and maintain deep knowledge of B2B sales best practice — from team structure and incentive design to pitch development and customer journey optimisation — and bring that into the product.
• Contribute to thought leadership and content marketing that demonstrates Collingwood’s expertise in commercial value creation.
• Speak at or host events (digital and in person) in line with the firm’s marketing strategy.

Collaboration and teamwork

• Collaborate with Strategic Advisers, Client Directors, and Associate Advisers to ensure sales workstreams are delivered on target and integrated with the wider engagement.
• Share delivery lessons and product ideas with colleagues, contributing to a culture where the whole team benefits from individual experience.
• Provide clear briefs and regular updates to the programme delivery team throughout each engagement.
• Host regular team check‑ins to keep all contributors aligned and on track.

Team, personal and professional development

• Coach and develop Associate Advisers through on‑the‑job guidance, feedback, and knowledge sharing.
• Build knowledge of Collingwood’s wider advisory methodology and delivery approach, enabling effective collaboration across workstreams.
• Take a proactive approach to own development, identifying gaps in knowledge and seeking opportunities to grow skills and contribute to Collingwood IP.
• Provide fair, timely, and constructive feedback to colleagues to support performance and development.

About You

Essential

• Demonstrable expertise in B2B commercial and sales strategy, with a track record of improving sales team performance in practice.
• Experience designing or transforming sales structures, processes, or incentive schemes within a business or as an external adviser.
• Strong workshop design and facilitation skills: able to lead client sessions that result in clear decisions and actionable outputs.
• Proven ability to originate new business: identifying prospects, leading discovery conversations, writing proposals, and closing engagements independently.
• Comfortable owning a pipeline and being accountable for BD outcomes, not just delivery.
• Experience developing advisory products, frameworks, or tools — whether in a consulting firm, as a practitioner building internal capability, or both.
• Ability to document and systematise delivery knowledge so that others can use it, not just the person who built it.
• Confident presenter and communicator: able to build credibility quickly with founders and senior leadership teams.
• Experience working as a consultant, adviser, or specialist practitioner delivering structured engagements with defined outputs and timelines.
• Highly organised; able to manage concurrent client, BD, and product workstreams without losing quality in any of them.
• IT literate.

Preferred

• Direct experience in B2B media, with particular interest in candidates who have worked with subscription, membership, or business information businesses.
• Experience across more than one of the following areas: sales narrative and pitching, customer journey design, commission and incentive scheme design, rebooking strategy.
• Previous experience in a commercial leadership role (e.g. Sales Director, VP Commercial) within a B2B information or events business.
• Experience in consulting, either independently or in a firm.
• Experience productising advisory or consulting services: turning delivery experience into reusable, scalable products.
• Familiarity with the commercial dynamics of scaling businesses preparing for investment or a capital event.

Attributes

• Proactive communicator; humility, empathy, and strong listening skills.
• Persuasive and direct; able to challenge clients constructively and get them to act on recommendations.
• A team worker who shares potential problems with colleagues to find better solutions.
• Energised by variety: comfortable moving between strategic diagnosis and hands‑on delivery.

Why Collingwood?

At Collingwood, everyone plays a role in shaping the future of the business. We are a values‑driven team that thrives on collaboration — with each other and with our clients. This role is based out of our Central London office on a hybrid basis. It is a permanent, full‑time position offering real impact for ambitious businesses alongside the flexibility to suit your career stage. Ready to help us scale? Apply now.

Key Information

• Reports to: Client Director
• Working location: Hybrid (UK) (3+ days in office)
• Department: Advisory
• Hours: Full time