Job Description
About Gladly
For business leaders who want to get AI right, Gladly is the only customer experience AI that delivers the cost savings they need AND the customer devotion that drives lasting business value. With over a decade of singular CX focus and trusted by the world’s most customer-centric brands including Crate & Barrel, Breeze Airways, and Ulta Beauty, Gladly was designed for devotion, not deflection: purpose-built to engage customers and turn every conversation into lasting relationship equity. The result is experiences that are radically personal and effortlessly scalable, emotionally intelligent and operationally efficient.
At the heart of our simply powerful platform, Gladly maintains one continuous conversation across all channels while striking the perfect balance of AI and human connection. With 300M+ conversations powered globally, $510M+ cumulative cost savings delivered for customers, and a 65% increase in CSAT scores, this is a team where your work has real impact at scale. Learn more at www.gladly.ai.
The Team
You will join a high-impact team of strategic account managers who own revenue outcomes across our Enterprise accounts. We are a group of commercially-driven experts fueled by underdog grit and a commitment to mutual accountability. We don’t just manage accounts; we operate as the CEO of our book of business—driving net dollar retention, identifying expansion opportunities, and delivering measurable ROI for B2C leaders.
The Opportunity
We are looking for a Strategic Account Manager to own a portfolio of Enterprise accounts across the install base. This is a quota-carrying, revenue-accountable role where you will drive renewals, expansion, and net dollar retention across a higher-volume book of business.
The ideal candidate is a commercially-minded operator who thrives in a fast-paced environment, can manage multiple accounts simultaneously, and knows how to turn customer relationships into revenue growth. You are proactive, organized, and relentless in identifying opportunities to expand Gladly’s footprint within your accounts.
What You’ll Do
- Revenue Ownership: Carry a net dollar retention quota. Own the full renewal cycle, proactively identify and close expansion and cross-sell opportunities, and drive adoption of Gladly’s AI products across your portfolio.
- Account Planning & Prioritization: Build efficient account plans that balance high-impact strategic engagement with portfolio-wide coverage. Identify key accounts for deeper investment and develop playbooks for scalable growth.
- Customer Engagement: Lead QBRs, renewal discussions, and strategic conversations with VP and Director-level stakeholders. Translate platform value into business outcomes that support retention and growth.
- Commercial Negotiation: Manage renewal and expansion negotiations with confidence. Navigate procurement and approval processes efficiently across a larger book of business.
- Product & Solutions Expertise: Leverage knowledge of Gladly’s platform and Customer AI capabilities to recommend solutions that drive efficiency and customer value. Position AI adoption as a strategic expansion lever.
- Cross-functional Collaboration: Partner with Sales, Product, and CX teams to advocate for the Voice of the Customer and ensure alignment on account priorities and timelines.
What We’re Looking For
- Experience: 5+ years in a quota-carrying, client-facing role (Account Management, Customer Success with commercial ownership, or Install Base Sales) within a SaaS environment.
- Revenue Track Record: Proven success owning renewal and expansion targets. Experience managing five-to-six figure commercial cycles.
- Portfolio Management: Strong ability to manage a higher-volume book of business without sacrificing quality of engagement or commercial rigor.
- Commercial Mindset: You see customer success and revenue growth as inseparable. Every interaction is an opportunity to deepen value and expand the relationship.
- Operational Discipline: Excellent organizational skills and the ability to prioritize effectively across competing demands in a fast-paced environment.
- Ownership & Initiative: A proactive, “CEO of your book” mindset. You identify risk early, surface opportunities independently, and drive action without waiting for direction.
- Underdog Grit: A willingness to learn, adapt, and strive for excellence in an environment that values transparency and winning as one team.
Why Join Gladly?
Gladly is redefining customer experience AI — designed for devotion, not deflection. We put people at the center of everything we build, from our platform to 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
- A company where AI is not a buzzword. We build AI products and we expect our team to use AI tools daily
We’re a team that believes in transparency, collaboration, and the idea that the best work happens when talented people genuinely enjoy working together. Top talent, good vibes, no politics. If this role excites you but you don’t meet every qualification, we still encourage you to apply. The perspectives and experiences you bring matter more than checking every box.
