Enterprise Account Executive - US
About Gladly:
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. Learn more at www.gladly.ai.
We are in search of an Enterprise Account Executive that will help to open-up our presence in the North American market. 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. 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.
What You'll Do:
- 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
- Additional Sales responsibilities, as needed
Requirements:
- 5+ years of enterprise sales experience driving adoption of emerging technologies with a consultative, solutions-oriented sales approach
- A track record of managing complex sales cycles and securing strategic deals by understanding multifaceted technical requirements and crafting tailored solutions
- Demonstrated ability to navigate dynamic stakeholder ecosystems, building consensus and providing innovative solutions to disparate groups
- Proven track record of consistently meeting and exceeding sales quotas
- Strong track record of building pipeline, running discovery, and managing deals end-to-end without relying on a sales engineer
- Skilled at distilling complex ideas into simple, actionable narratives, both in writing and in live conversation, with technical and non-technical audiences
- Known for your collaborative style, you bring in product, marketing, legal, or leadership at the right time and with clear context
- Experience working in early-stage or founder-led sales environments, where feedback loops are short and product-market fit is still evolving
- Consistently earn trust across internal teams and customer stakeholders by showing up prepared, asking smart questions, and following through
- Proactively adapt to shifting customer needs, competitor movements, or product changes without waiting for top-down direction
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.
Compensation:
$229,500 to $270,000 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
Want more jobs like this?
Get jobs in Flexible / Remote delivered to your inbox every week.
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.
Perks and Benefits
Health and Wellness
Parental Benefits
Work Flexibility
Office Life and Perks
Vacation and Time Off
Financial and Retirement
Professional Development
Diversity and Inclusion