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.
You will join a high-impact team of strategic account managers who own revenue outcomes across our most valuable Enterprise accounts. 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 OpportunityWe are looking for a Senior Strategic Account Manager to own a portfolio of 7–10 high-touch Upper Enterprise accounts. This is a revenue-accountable role where you will be the single owner of your book; responsible for renewals, expansion, and net dollar retention.
The ideal candidate has a track record of growing strategic customer accounts. You are someone who can command a room with C-suite stakeholders, relentlessly identify white space business opportunities, and translate Gladly’s Customer AI capabilities into revenue-generating outcomes for both the customer and Gladly. You are an expert at building trusted relationships, internally as a cross-functional leader and externally across various levels of an organization, that enable you to drive performance and great win-win outcomes.
What You’ll Do- Revenue Ownership: Carry a net dollar retention target across your portfolio. Own the full renewal cycle, drive cross-sell revenue through increasing AI product adoption, and proactively identify and close upsell revenue.
- Strategic Account Planning: Build and execute comprehensive account plans that map white space, identify key stakeholders, and align Gladly’s platform with each customer’s strategic priorities and business outcomes.
- Executive Engagement: Own all executive-level relationships and engagement. Lead Customer QBRs and EBRs independently,translating platform data into business outcomes that resonate with executive stakeholders ranging from CIOs, CTOs, CDOs, and COOs to VPs of CX (Support, Service, etc.), VPs of IT, and beyond.
- Commercial Negotiation: Lead complex, multi-stakeholder renewal and expansion negotiations. Navigate procurement, legal, and executive approval processes with confidence and urgency.
- Product & Solutions Expertise: Leverage deep knowledge of Gladly’s platform and Customer AI capabilities to recommend solutions that drive radical efficiency and customer devotion. Position Gladly’s AI products as strategic investments, not line items.
- Cross-functional Leadership: Partner closely with Sales, Product, and CX teams to ensure the Voice of the Customer shapes our roadmap. Hold internal and external stakeholders accountable to timelines and commitments.
- Experience: 8+ years in a quota-carrying, client-facing role (Strategic Account Management, Install Base Sales, or Expansion Sales) within a SaaS environment. Enterprise high-touch experience is required.
- Revenue Track Record: Demonstrated success exceeding net retention plus expansion targets, including six-to-seven figure renewals and commercial negotiations.
- Portfolio Management: Strong ability to lead and manage through higher-volume Book of Business periods without sacrificing quality of engagement or commercial rigor.
- Ownership & Initiative: A proactive, “CEO of your book” mindset. You don’t wait for direction. You anticipate customer needs, identify risk, and drive action independently.
- Executive Presence: The ability to hold your own with C-suite stakeholders (think: VP of CX at a Fortune 500 retailer). You command a room, not just present in one.
- Commercial Mindset: A relentless focus on growing revenue. You see every customer interaction as an opportunity to identify white space and drive commercial outcomes.
- Customer Obsession: You care deeply about your customers, helping them achieve their goals, and making them raving fans of Gladly in the process. Customer devotion and commercial performance aren’t at odds, they fuel each other.
- Strategic Thinking: Proven ability to build multi-threaded account strategies, navigate complex organizational hierarchies, and create actionable roadmaps tied to impact.
- Underdog Grit: A willingness to learn, adapt, and strive for excellence in an environment that values transparency and winning as one team.
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.
Gladly Compensation & Benefits Highlights
The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about Gladly and has not been reviewed or approved by Gladly.
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Healthcare Strength — Health coverage is described as comprehensive, spanning medical, dental, vision, life, disability, EAP, and wellness support. Plan details highlight low in‑network copays and substantial employer-supported coverage across core benefits.
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Parental & Family Support — Policies include 16 weeks of paid parental leave for all parents, plus adoption assistance and fertility benefits. Feedback suggests these supports are a standout element of the package.
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Leave & Time Off Breadth — Unlimited vacation, paid holidays, and paid sick time are standard. Flexible schedules and a remote‑friendly setup further enable meaningful time‑off usage.
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What We Do
Uniquely powered by Customer AI, Gladly is the only CX platform that puts the customer —not tickets —at the center of every conversation. Trusted by the world’s most customer-centric brands, including Crate & Barrel, Ulta Beauty, and Tumi, Gladly delivers radically efficient and radically personal experiences. Gladly was built for B2C leaders who refuse to compromise on operational efficiency or experience. With Gladly, every conversation feels uniquely tailored and instantly responsive, emotionally intelligent and operationally precise, deeply personal and effortlessly scalable. At the heart of our simply powerful platform is Gladly Customer AI —uniquely designed to maintain a single, continuous conversation across all channels while striking the perfect balance of technology and human connection. Gladly is loved and trusted by hundreds of world-class brands to deliver award-winning experiences and drive serious results —240 million conversations powered by Gladly Customer AI, $510M cumulative cost savings across brands using Gladly, and a 65% increase in CSAT scores. Customer experience isn’t broken—it’s just built on the wrong foundation. Gladly reimagines CX with AI that gets it right.
Why Work With Us
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.
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