Enterprise Account Executive - Midwest


Midwest, , US
  • Job Type: Full-Time
  • Function: Sales
  • Industry: Technology
  • Post Date: 05/02/2021
  • Website: gladly.com
  • Company Address: 201 California St Suite 1400, San Francisco, CA, 94111

About Gladly

Gladly is a Radically Personal Customer Service Platform. Unlike legacy customer service platforms that are case centric, only Gladly is designed with people at the center and uniquely enables a single lifelong customer conversation from voice to modern messaging. Gladly powers some of the most innovative consumer companies like JetBlue, JOANN, and TUMI to deliver exceptional customer experiences and makes customer service a competitive advantage.

Job Description

An amazing customer service experience can make your day. But a really terrible one can also ruin it. No one likes to be treated like a ticket or case number. But these days, even if companies want to build authentic relationships with their customers, they can’t – their systems don’t enable it. That’s where Gladly comes in - we believe exceptional customer service is about putting people at the center, not cases or tickets, to let the world's greatest brands treat their customers as people, nurture relationships, and ultimately drive revenue as a result. Enterprise companies want to build empathetic relationships with their customers and Gladly provides a platform that empowers companies to have conversations across any channel, from text to tweet.

We are in search of an Enterprise Account Executive to be based out of the Midwest territory. Successful Account Executives will have a proven track record of building strong pipelines and rapidly closing business. Our ideal candidates are self-directed and thrive in an early stage environment, apply a consultative approach, and excel in setting and surpassing customer expectations. This person has a strong passion for customer success and will focus on obtaining and retaining referenceable customers. We’re looking for someone who has strong execution skills, is focused, responsible, and accountable. As an entrepreneur, our account executive understands the demands of an early-stage company and works with the team in a collaborative, problem-solving manner. We’re looking for someone who has strong execution skills, is focused, responsible, and accountable. Your activities in prospecting and closing will be supported by strong lead generation and awareness efforts.

Responsibilities and Expectations

  • Achieve and exceed sales goals
  • Build and grow sales pipeline
  • Present value proposition to executive level prospects
  • Establish and achieve prospecting and business development goals
  • Collaborate with our Marketing and Sales Development organizations to expand pipeline and increase sales velocity
  • Uncover and convert prospects to clients through cold calling, managing pre-qualified opportunities, conducting discovery, and building relationships
  • Able to act as lead sales person as well as potential to lead a team as the company grows
  • Serve as a mentor and motivator to the team
  • Potential to attract, motivate and manage a world class team
  • Willing to travel regionally to represent the company


  • Deep experience selling cloud based SaaS products from C-level to individual and team stakeholders
  • Proven track record of consistently meeting and exceeding sales quotas
  • Ability to demonstrate flexibility and comfort in fast-paced sales environment
  • Significant direct sales experience with SaaS solutions
  • Excellent verbal and written communication skills
  • Team player with collaborative personal style
  • An entrepreneurial mindset; startup experience highly preferred
  • Integrity and ethics are critical
  • Excellent interpersonal and leadership skills
  • Inquisitive, thorough problem solver
  • Highly motivated, smart risk taker
  • Adaptable to changing market conditions and customer requirements
  • Balanced approach to problem solving between analytical and intuitive
  • Ability to travel

At Gladly we value:

Putting people first We built our product putting people at the heart of it all. And we’ve taken the same approach to building our company.

Focusing on the customer We treat our customers’ goals as our own, and we work hard to achieve them.

Being humble and hungry We applaud initiative and value leadership—but we also believe that nobody is above emptying the dishwasher.

Always learning Everyone’s personal best is ahead of them. Seeking new ways to grow is what keeps us motivated.

Owning it We encourage everyone to seek and share feedback, take calculated risks, and learn from their mistakes.

Communicating it With an open and transparent culture, collaboration becomes a lifestyle and everyone has a voice

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
  • Wellness stipend

About Us

Founded in 2014 by a team of repeat entrepreneurs with multiple successful exits, Gladly is reinventing customer service. By managing customers instead of tickets, we are disrupting a $70B market and are proud to count JetBlue, Warby Parker, Crate&Barrel 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 full 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.

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