Enterprise Customer Success Manager

Remote, US

About Gladly:

Gladly, the customer-centered AI customer support platform is built around people, not tickets. Unlike traditional ticket-based customer support solutions, our software helps brands deliver radically personal service at scale by integrating every channel—voice, email, SMS, chat, social messaging, and self-service—into a single, lifelong conversation stream. Companies like Allbirds, Bombas, Crate & Barrel, and Warby Parker use Gladly to create exceptional customer experiences, transforming everyday customer interactions into lasting connections. 

Gladly is a fully distributed company that embraces remote work and believes in flexibility, innovation, and inclusivity. We foster a collaborative, inclusive culture that prioritizes growth, DEIB, and meaningful connections. At Gladly, people are at the heart of everything we do.

As an Enterprise Customer Success Manager on the Gladly Customer Success team, you are responsible for building long-term strategic relationships, increasing product adoption and ensuring seamless renewals. You will be responsible for our largest customers. You'll work closely with key stakeholders to understand their business objectives and translate that into how best to use Gladly to help them achieve their intended outcomes. As a customer advocate, you'll liaison between our customers and our internal organization, ensuring that their needs and/or requirements are communicated and managed throughout Gladly while balancing these asks with the business needs. You’ll gather customer feedback and product requests while focusing on aligning customer adoption with our current product capabilities. You will own a retention and renewal number on a quarterly and annual basis, as well as help to expand and/or up-sell, as appropriate. In addition to traditional CSM responsibilities, you will help to define and iterate how we approach various programs, customer communications, customer engagement, and strategic planning initiatives.

What you’ll do:

  • Own the success of Gladly customers in achieving the value of relationship-based customer service using the Gladly platform.
  • Build lasting relationships through consistent engagement with customer executives and managers to instill understanding of product vision, value proposition and features. Proactively engage clients to drive product adoption and optimal product experiences.
  • Partner with Sales Account Executive to develop and execute on account plans, ensure alignment within Gladly teams on account strategy. Develop & maintain relationships with other key internal customer champions, including engineering, product and marketing leadership to help strategically guide the direction of the product based on voice of the customer feedback.
  • Serve as a product expert for customers, including deployment best practices as well as configuration of product settings/rules to address customer business and technical needs.
  • Act as a strategic advisor with the ability to make recommendations on how to best leverage the Gladly platform as well as improve processes that may fall outside of the contact center.
  • Resolve account issues quickly, leveraging resources from across the company as needed.
  • Contribute to Gladly's Customer Success program development, strategic planning, and customer engagement approach to drive consistency and scale as the company grows.
  • Participate in pre-sales activities with prospective customers such as meetings, workshops, and webinars.

Required Skills/Experience

  • Previous experience in a B2B client facing role (sales engineering, consulting, professional services, CSM, or technical account management).
  • Previous experience implementing SaaS software applications and/or providing technical and strategic advisory services.
  • Genuine passion for building and maintaining strong relationships with a diverse set of internal and external stakeholders, from engineering, product, marketing, etc.
  • Entrepreneurial. Highly Ethical. Hands on. Passionate. Curious. Persistent. Creative. High standards for personal productivity. Enthusiastic about building Customer Success in a start-up environment.
  • Great communication skills - able to provide clear & concise guidance through emails, over the phone, or in person, with a casual and confident tone.
  • Excellent organization, project management, time management skills is a must.
  • Able to gain consensus and get business and technical teams to work together toward timely issue resolution.
  • Able to build and support a business case to customer teams.
  • A strong awareness of business processes and ability to translate business processes into enterprise application implementations.
  • Effective team player dedicated to continuously improve upon our process of advocating for the customer.
  • Innately understand how to balance advocacy for Gladly and the customer by looking for win:win outcomes.
  • Comfortable and willing to engage on-site with customers where needed.

Nice to have:

  • Previous experience with a major systems integrator and/or cloud-based/SaaS solution offerings company.
  • Expertise of customer support software and/or telephony processes.

Compensation
$103,000 to $160,000 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.

Why Join Gladly?

At Gladly, we’re not just building software—we’re transforming an industry. We take a people-first approach, both in our product and our culture. When you join us, you’ll enjoy:

  • Competitive salaries, stock options, and comprehensive benefits
  • Generous paid time off, parental leave, and home office stipends
  • A fully remote work environment with opportunities for in-person team gatherings
  • A strong commitment to professional growth and an inclusive workplace where diverse perspectives thrive

At Gladly, we believe in challenging the status quo, celebrating grit, and striving for excellence. We thrive as a team by embracing transparency, collaboration, and a customer-first mindset. If this role excites you but you don’t meet every qualification, we still encourage you to apply. Diverse perspectives and experiences are the cornerstone of our success.

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