Director of Sales

The opportunity

Help Scout is looking for a seasoned Director of Sales to join our team and report to our CRO, Andrea Kayal. Help Scout focuses on supporting small businesses (SMBs).

Today our product drives a portion of our New ARR, but our Sales team is a critical function in helping our larger customers better understand our offering. As the Director of Sales, you will play a pivotal role in helping us gain marketshare and grow the footprint of our uniquely lovable brand.

About the role

• Your mission is to manage our sales team of 3 AEs and work hard to help them grow and excel in their careers.
• You’ll be responsible for maintaining a results-orientation mindset — you’re not satisfied unless we’re exceeding our sales targets.
• You’ll track and communicate out sales performance KPIs, including trends in win rates, ACV, sale cycle times, and rep productivity as well as conduct pipeline reviews to produce accurate sales forecasts.
• You’ll collaborate closely with Marketing and Product leaders to ensure adequate pipeline coverage, an alignment of GTM tactics, and to ensure prospect needs are reflected on the roadmap. 
• You stay in the loop on trends in category-specific landscapes to improve sales tactics and will always be looking for better ways our sales team can close deals. 

About you

• You have about 7 years of proven sales experience with a consistent track record of meeting or exceeding targets and driving sales processes from plan to close.You follow a sales methodology that fosters a standardized process for product demos, deal management, and close plans.
• You have exceptional communication skills, both verbal and in writing, and can present clearly and influence all levels of the organization.
• You are a sales leader that is motivated by helping customers truly gain value over the long term — winning isn't just about closing deals.
• You’re a fast learner and get excited to go deep into the weeds about B2B SaaS products and services in order to better sell to customers. 
• You are excited to be part of a remote-first organization. You feel well-equipped and eager to manage the tradeoffs with enthusiasm, highly organized information, and excellent communication skills (sync and async).

About the team

Our Sales team is part of what we call our Revenue Org — it also includes Brand, Product Marketing, Partnerships and Account Management.

You’ll manage our three AEs, and partner with other teammates in the Revenue Org like our VP of Marketing, Kristen Bryant Smith and our Director of Product Marketing, Alison Charles.