Opened 7 days ago Remote Job

Regional Director of Enterprise Sales - US

About Gladly:

Gladly is the only customer service software built around people, not tickets. Gladly applies AI differently, to help brands deliver radically personal customer service at scale, enabling consumers to help themselves and turning customer service agents into heroes by making them more productive. Every conversation starts with a real-time understanding of the customer. With every channel built-in – voice, email, SMS, chat, social messaging, self-service – companies have one, lifelong conversation stream with their customers. The world’s most loved brands including Allbirds, Bombas, Crate & Barrel, Ulta Beauty, and Warby Parker leverage Gladly to build lifelong loyal customers. 

Our team loves working at Gladly because of its people, continuous growth opportunities, all in commitment to DEIB, collaboration, and culture. 

Why We Need You

The Director of Enterprise Sales is a critical sales leadership role for Gladly. Reporting to the VP of Enterprise Sales, you’ll own the day-to-day responsibilities of building, leading and growing a revenue organization that will serve some of the leading retail brands in the world who are looking to innovate and change the way they deliver personalized service and support at scale.

You will play a central role in expanding Gladly’s presence across the U.S. and Canada. You will use your deep industry knowledge of customer service and contact center needs, network and expertise in closing complex deals and help to enable and drive a high-performance team to execute our go-to-market initiatives.

As the Director of Enterprise Sales, you'll get to...

  • Directly contribute towards building and growing our company pipeline and revenue

  • Motivate and direct a top-performing Enterprise sales team and guide them to succeed at both exceeding revenue targets as individuals and as a collective team

  • Collaborate closely with our Marketing and Sales Development organizations to expand pipeline and increase sales velocity

  • Develop and implement go-to-market strategies tailored to specific target verticals and/or companies; partner closely with Marketing and other functions to architect and execute a well-oiled machine to drive pipeline conversion

  • Set team and individual KPIs and hold your team members accountable, while creating an environment that brings out the best in everyone

  • Implement tools and scalable processes to nurture the pipeline, track and report progress, and accurately forecast revenue

About You

  • You have 2-3 years experience managing a Enterprise sales team with 4-7 Account Executives.

  • You have experience with MEDDPICC and other sales methodology frameworks.

  • You are self-directed and thrive in an early-stage fast-paced sales environment

  • You apply a consultative approach and excel in setting and surpassing customer expectations

  • You have a proven track record in selling sophisticated and innovative solutions to C-level and other key decision-makers

  • You have deep domain experience and understanding of the customer service and support market, and can provide authentic and credible insights into how customer service trends are changing and evolving

  • You are driven by customer success and will focus on obtaining and retaining referenceable customers

  • You have an existing network of key decision-makers for customer service within our target customers -- such as major retailers, direct-to-consumer, travel, and hospitality brands

  • You are passionate about leading teams with the innate ability to connect with and inspire your team to hit and exceed sales targets

  • You are adaptable to changing market conditions and customer requirements

Research has shown that individuals from marginalized groups are less likely to apply to jobs where they don't meet 100% of the criteria. Gladly values diversity of experience, so if you believe you have the right skill set, we welcome you to apply - even if you don't check every box in the job description. We're committed to an inclusive workplace and would love to see if you could be the next great addition to our team.


$325,000 - $350,000 per annum OTE (base + variable); equity, and benefits

For cash compensation, we set standard ranges for all U.S.-based roles based on function, level, and geographic location, benchmarked against similar stage growth companies. In order to be compliant with local legislation, as well as to provide greater transparency to candidates, we share salary ranges on all job postings regardless of desired hiring location. Final offer amounts are determined by multiple factors, including geographic location as well as candidate experience and expertise, and may vary from the amounts listed above.

Working at Gladly:

Putting people first is kind of our thing. Not only is it at the core of our product, but shapes our overall culture at Gladly—from our approach to hiring, to our benefits, and how we think about our place in the community.

We have embraced remote work and make it easy for our team to work from anywhere, but we also invest in opportunities to get the teams together in person regularly.

We have a strong work ethic, but value life outside of work, too.

Gladly Beliefs:

  • We win as one team: We believe the most important focus for us as a team is making the company successful.

  • We are successful when our customers succeed: We are committed to understanding the needs and expectations of our customers. We provide an exceptional product along with expertise and insight to help achieve their goals.

  • We believe in challenging the status quo: We know that our greatest strength is our ability to cultivate a growth mindset focused on reinventing customer service. 

  • We value underdog grit: Success isn't always about having the most resources or the most experience; it's about having the determination and grit to keep pushing forward especially when it’s hard.

  • We strive to make every shot count: We will never have enough “shots on goal” so we strive to make every project, feature, customer presentation, the best it can be.

  • We embrace transparency: We know the best outcomes come from collaboration followed by communication of and commitment to the decision.

Our focus is on people and that starts with our employees. As an employee you can count on:

  • Competitive salaries, stock options

  • Medical, Dental, Vision and Life insurance

  • Generous paid time off

  • Generous paid Parental Leave

  • 401K

  • Flexible Spending Accounts

  • Home office stipends

Founded in 2014 by a team of repeat entrepreneurs with multiple successful exits, Gladly is reinventing customer service. By focusing on customers instead of tickets, we are disrupting a $70B market and are proud to count Crate and Barrel, Warby Parker and many other innovative brands as customers. Gladly has raised over $110M from Greylock Partners, NEA, GGV Capital, Glynn Capital and JetBlue Tech Ventures.

Gladly has made the decision to become a fully distributed company, allowing employees to live anywhere in the United States, and candidates to come from nearly any geographical region. That said, we also highly value our collaborative and creative culture and commit to meeting in real life as a company at least once per quarter when it is safe to do so.

Don't let this one get away.