Our role As Head of Sales, you’ll lead from the front—setting the standard by generating leads, delivering powerful demos, and closing deals. Your success will directly drive Chalkstring’s growth, and in return, you’ll enjoy a £100k OTE package and significant opportunities for career progression. At Chalkstring, we support specialist contractors—the unsung heroes who build our schools, hospitals, homes, and infrastructure. These businesses face some of the highest risks of insolvency due to difficult industry practices, but with the right tools, they can thrive. Chalkstring provides the cost management software they need to run profitable, sustainable businesses. By giving more contractors access to Chalkstring, you won’t just help our business grow—you’ll empower these vital businesses to succeed, strengthening UK construction and boosting the economy. This is a rare opportunity to join a fast-growing company at a pivotal moment, where your work will make a real difference to both our business and the industry we serve. Drive sales growth Hitting and exceeding sales targets | Own sales conversion rates by enhancing outreach and demo strategies to optimise close rates, establish predictable run rates, and exceed KPIs. Building pipeline | In addition to responding to inbound leads, developing and maintaining a sustainable pipeline of prospects using a mix of calls, emails and social media channels. Delivering software demonstrations | Conducting impactful software demonstrations that showcase the value of our products to potential clients. Negotiating contracts | Engaging in strong contract negotiations to secure deals, capitalise on upsell opportunities and drive revenue growth. Shaping the sales strategy | Refining go-to-market messaging to improve conversion rates and developing scalable sales processes and systems to support future team growth. Drive innovation | Bring fresh ideas and new technologies to the table, from AI tools to streamline processes to creative approaches to closing deals. Further your career Deliver results and you'll have the opportunity to: Build and lead a sales team. Have a seat at the table as part of the executive strategy team. Play a key role in our ambitious growth plans. Earn share options and share in the success you help create. Requirements Proven B2B SaaS sales experience | Proven track record in B2B sales, particularly with complex technical products and ideally in construction Goal-oriented | Demonstrated ability to achieve KPIs and sales targets Self-motivated | Capable of working independently Effective communication | Excellent communication skills with strong attention to detail Problem-solving skills | Ability to think laterally, come up with viable solutions and adapt to change Senior-level engagement | Skilled in engaging effectively with prospective clients at a senior level Resilience | Possess the ability to deal with challenges, even when the chips are down Passionate | Display a positive, outgoing & passionate demeanour Analytical and data-driven mindset | Capable of tracking, interpreting, and using sales metrics to refine strategies Eligibility | Must live in and be eligible to work in the UK Transport | Hold a full clean driving license and have access to a car How to apply To apply for this role, please submit your CV to hello@chalkstring.com. We look forward to receiving your application. Join us in driving our continued growth and be part of our exciting journey at Chalkstring.
