PACKAGE
£100k OTE and uncapped commission
Uncapped commission & bonus structure
Future share options
Permanent role
27 days annual leave
LOCATION
Midlands-based role, with travel UK-wide for prospect meetings
TRAINING
Full product training provided
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 drive Chalkstring’s growth, and you’ll be rewarded with a competitive package and significant opportunities to advance your career.
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 in the industry, 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.
Hit and exceed sales targets | Own sales conversion rates by experimenting with and improving outreach and demo strategies to optimise closing rates, establishing predictable run rates, and exceeding KPIs.
Building pipeline | In addition to working with inbound leads, developing and maintaining a sustainable pipeline of prospects using a mix of calling, 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 | P roven 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 remotely with minimal supervision
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
- Analytical and data-driven mindset: Capable of tracking, interpreting, and using sales metrics to refine strategies, optimise conversion rates, and establish predictable run rates.
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
We look forward to receiving your application. Join us in driving our continued growth and be part of our exciting journey at Chalkstring.
#J-18808-Ljbffr
