Upskill Digital

Commercial Director

Join Upskill Digital as they are looking for a Commercial Director

About UpSkill Digital

UpSkill Digital is a leading organisation in the world of Skills and Inclusion. Since 2015 we’ve built some of the world's largest award-winning digital skills, talent and inclusion programmes empowering over 650,000 people globally partnering with the likes of Google, Walmart, HSBC, and TikTok.

We are passionate about tackling the skills and representation in business, supporting companies to create equitable career pathways to boost progression and develop relevant skills for the future workplace.

As a company, we have big plans, to continue our expansion and growth in the UK, and continue to roll out our programs targeting the US, Europe and Asia-Pacific and Sub-Saharan Africa markets. We are continuing to grow and want to build an iconic company recognised for its innovative approach to delivering scalable learning.

About the challenge

We are looking for an exceptional Commercial Director with a successful track record of creating, defining and operationalising go-to-market strategies, managing complex sales cycles, and are excited by the opportunity to drive forward UpSkill Digital’s international growth. You have experience shaping & defining commercial propositions, driving ROI and Value through our products and are excited by the opportunity to shape our SaaS proposition as we shift from a managed service. You have a proven track record of winning and delivering international commercial work in the global B2B workforce education space.

You’ll be part of the company’s executive leadership team, you will work closely with our CEO and wider team to develop UpSkill Digital’s commercial strategy, drive a healthy sales pipeline and ensure successful delivery of our learning solutions to clients.

You have been highly successful in achieving financial targets and strategic objectives with extensive experience in managing key client relationships, reviewing and closing strategic, multi-year opportunities across multiple territories worldwide.

You will be the main driver of sales enablement as it relates to sales tools and processes, managing our lead generation/sales development technology stack and maintaining sales data in (CRM) and other software programs.

Main duties

  • Working closely with the CEO and company leadership to determine overall company strategy
  • Responsible for translating the company strategy into the end-to-end commercial strategy to create a coherent revenue-generating function which delivers on the growth targets of the company
  • Take a lead role in drafting wider group commercial partnerships with partner organisations
  • Exploring new business opportunities, and supporting the commercial teams in negotiations with key clients.
  • Creating and overseeing the right processes between teams in the Commercial function to ensure the right collaboration occurs, and to ensure efficiency in the revenue-generating function
  • Deliver accurate revenue projections and enhance predictability, enabling improved business planning and strategic development.
  • Develop and manage accurate revenue forecasting models, providing regular reports and analysis to the executive team
  • Establishing and implementing go-to-market strategies across all UpSkill products
  • Managing and allocating a financial budget to maximise Commercial team performance
  • Lead and inspire the sales and channels revenue teams, setting clear revenue targets and driving performance to exceed goals
  • Monitor and evaluate key performance indicators (KPIs) to assess revenue growth, sales effectiveness, and market penetration
  • Instil a culture of productivity and high performance by developing a commercial mindset across our sales professionals
  • Evaluate and optimise delivery cost models to ensure business efficiency and profitability.
  • Implement effective sales methodologies, enablement programs, processes, and performance metrics to optimise the sales pipeline and ensure
  • Oversees the entire customer journey, from lead generation and acquisition to retention and expansion to understand customer needs, identify upsell and cross-sell opportunities, and drive expansion revenue
  • Develop and maintain prospecting records via our CRM (HubSpot) to produce sales reports (monthly & quarterly) including activity progress and sales achievement forecasts


  • You have 10+ years of experience in a sales/commercial position, selling complex B2B Learning solutions, social impact programs, or D&I consultancy to Enterprise / Medium size businesses
  • 2+ years experience at Director level and have reported into C-suite
  • You have been instrumental in driving revenues for a business of this nature
  • Experience dealing with, and successfully influencing high level executives
  • You have experience with typical sales and marketing tools (e.g Hubspot)
  • You have workedin a start-up, scale up or agency environment
  • Availability to travel for face-to-face meetings internationally

Location: UK based - We currently do not offer sponsorship

Our values

We own it: The impact of what we do is what fuels us, so we take full ownership of our work and our relationships to ensure we deliver with pride.

We fix each other’s crowns: Whether it’s our team, our clients or our partners, we support each other to be at our best, always striving to be there when you need an uplift.

We strive to grow: Every person we meet has something amazing to offer this world, so we celebrate our differences and foster a mindset of curiosity, inspiring each other to greatness.

We work sustainably: We adopt mindful practices and prioritise the health of each other and our environment, ensuring our impact is always positive.

Does this sound like you? Then get involved!

We would love to get a feel for your approach and personality, so if you feel you would be a great fit, please submit your application.