PACKAGE
Competitive salary split 50/50 basic 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

Job description & responsibilities

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.

Drive sales growth

• 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 | 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 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

• Passionate | Display a positive, outgoing & passionate demeanour

• 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

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.