Squarespace

Compensation

Full Description

About the position Responsibilities • Build Your Team: Partner with leadership to recruit, hire, and onboard a high-performing team of Account Executives, establishing a culture of success, accountability, and consultative selling from day one. • Define the Playbook: Architect and implement the sales strategy and playbook for cross-sell and expansion, including identifying buying signals, developing outreach cadences, and articulating value propositions for our integrated product suite. • Lead from the Front: Provide daily, hands-on coaching to your reps on the frontlines. You will be deep in the details of the business—joining calls to help move deals forward, workshopping deal strategy, and providing real-time feedback to develop your team's skills. • Drive Expansion Revenue: Lead your team to consistently meet and exceed monthly and quarterly expansion sales targets. You will be responsible for accurate forecasting, meticulous pipeline management, and reporting to sales leadership. • Collaborate Cross-Functionally: Partner closely with our Customer Success, Marketing, and Product teams to ensure a seamless customer experience, identify expansion opportunities, and provide critical feedback to inform GTM strategy. • Master the Tools: Champion the use of our sales tech stack to drive efficiency and leverage data for coaching and strategic decision-making. Requirements • 5+ years of experience in B2B SaaS sales, with at least 2-3+ years in a sales management or team lead role. Preferred experience should be in an Account Management, Acquisition sales, or dedicated expansion/cross-sell role within a high-velocity SMB environment. • Proven track record of success in building and scaling a team that consistently exceeds expansion revenue targets through cross-selling and upselling. You’ve successfully hired and developed top-performing AEs. • A deep "player-coach" mentality; you’re a leader who is passionate about daily coaching, call reviews, and being actively involved in your team's deals to get them across the finish line. • Experience in creating sales playbooks, processes, and methodologies from an early stage (i.e. Challenger). • Expertise in pipeline management, accurate forecasting, and using data to drive team performance. • Deep proficiency with Salesforce and modern AI-driven sales tools (e.g., Gong, Clay, Momentum, Onum). • Exceptional communication, leadership, and interpersonal skills. Proven track record of hiring high performers and managing effectively to structure top-performing teams. • A builder’s mindset—you are comfortable with ambiguity and excited by the challenge of creating something new. Benefits • A choice between medical plans with an option for 100% covered premiums including medical, dental, and vision • Supplemental Life and Disability Insurance plans • Fertility and adoption benefits • Headspace mindfulness app subscription • Global Employee Assistance Program • Retirement benefits with employer match • Flexible paid time off • 12 weeks paid parental leave and family care leave • Pretax commuter benefit • Education reimbursement • Employee donation match to community organizations • 8 Global Employee Resource Groups (ERGs) • Dog-friendly workplace • Free lunch and snacks • Private rooftop • Hack week twice per year