Vice President of Sales

Vice President of Sales, MeasureSquare

About MeasureSquare

MeasureSquare is the leading flooring takeoff and estimating software, trusted by contractors, estimators, and retailers for over 20 years. We help our customers move from manual processes, estimate faster, reduce waste, and win more jobs. We're a lean, high-growth team deeply committed to the success of the flooring and construction industry.

Role Description

As Vice President of Sales, you will design and execute the sales strategy and operations needed to achieve ambitious revenue and growth targets. You will lead our remote sales teams, build a repeatable sales process and playbook, and instill the operational rigor required to scale effectively. This role is responsible for continuously elevating our sales motion, spearheading key initiatives, and cultivating the strategic relationships and partnerships that will fuel our next phase of growth and transform our current momentum into a world-class sales organization.

Who You Are

You are a builder at heart with a bias to action – you move fast, seize opportunities, and know how to scale what works. You're comfortable with ambiguity and thrive in fast-moving environments, with the energy to build from the ground up, and the discipline to grow and sustain it long-term.

Key Responsibilities

• Strategic Revenue Leadership:

You will act as the bridge between executive strategy and sales execution. Own the sales strategy and execution to meet annual ARR targets. Translate high-level business goals into actionable benchmarks.

• Repeatable Sales Playbook Development:

Refine and scale a repeatable B2B SaaS sales playbook, improving qualification and win rates, and speeding up our deal cycle

• Remote Team Management:

Lead, mentor, and scale a distributed team of AEs and SDRs, fostering a culture of high performance and professional development across time zones.

• Operational Scaling and Benchmarking:

Partner with Sales Ops to drive strategic initiatives to scale up our sales org, including implementing performance benchmarks, defining clear accountability frameworks, and establishing rigorous sales forecasting models.

• Sales Operations and Enablement:

Work with Sales Operations Manager to monitor, understand, and manage key processes such as commissions and incentives, sales performance metrics and forecasting. Deliver monthly and quarterly updates to the executive team.

• Cross-Functional Collaboration:

Partner with Marketing, Product, and Customer Success to ensure a seamless end-to-end customer journey

Qualifications

• 10\+ years of sales experience, with at least 3-5 years in a sales leadership role.
• Proven track record of successfully managing and scaling high-performing remote teams
• Deep expertise with B2B SaaS solution sales. Expertise in navigating large, complex, multi-stakeholder deals
• Strong command of SaaS metrics (LTV, CAC, churn, pipeline velocity)
• Familiarity with the flooring industry or construction trades is a strong plus
• Proficient in CRM systems (Zoho, Salesforce, Hubspot) for pipeline management and data reporting
• Maintain a bias to action. We operate as a lean team where every move counts. You must be comfortable executing at a high level without layers of middle management