Full-Time

Enterprise Account Executive

Posted on 10/31/2025

Gladly

Gladly

201-500 employees

AI-powered customer service platform.

Compensation Overview

$229.5k - $270k/yr

+ OTE + base + variable

Remote in USA

Remote

Category
Sales & Account Management (2)
,
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
Responsibilities
  • 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

Gladly is a customer service software platform that uses artificial intelligence to improve interactions between customers and agents. It provides a subscription-based service that replaces the traditional ticket-based system by tying all communications to individual customers, enabling real-time, personalized service across channels. The platform includes AI-powered tools such as Hero AI Authoring, Hero AI Summaries, and Hero AI Replies to boost agent productivity, along with self-service options guided by brand policies. Customers can access help around the clock, and the system aims to reduce costs and inbound volume while preventing duplicate tickets. Gladly’s goal is to turn customer service interactions into personalized experiences that build loyalty and strengthen brand reputation.

Company Size

201-500

Company Stage

Late Stage VC

Total Funding

$208M

Headquarters

San Francisco, California

Founded

2014

Simplify Jobs

Simplify's Take

What believers are saying

  • AVP-led $40M funding accelerates AI-powered unified platform growth in 2025.
  • Riverwood's $55M round in December 2022 innovates people-centered service for Allbirds, Warby Parker.
  • G2 reviews praise Gladly's intuitive interface and multi-channel efficiency.

What critics are saying

  • Zendesk's AI Suite adoption across 200K customers pressures Gladly's $27.3M revenue.
  • Microsoft Copilot for Service bundles into Microsoft 365, undercutting Gladly's SMB pricing.
  • Customer concentration in Allbirds, Bombas, Ulta Beauty risks 15-20% revenue loss on churn.

What makes Gladly unique

  • Gladly centers platform on customers, not tickets, unifying lifelong conversations across channels.
  • Hero AI tools like Authoring, Summaries, and Replies boost agent productivity and personalization.
  • Gladly Sidekick from Thankful acquisition enables generative AI and no-code automation.

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Benefits

Health Insurance

Dental Insurance

Vision Insurance

Life Insurance

Generous paid time off

Generous paid Parental Leave

401K

Flexible Spending Accounts

Home office stipends

Stock options

Remote Work Options

Growth & Insights and Company News

Headcount

6 month growth

2%

1 year growth

4%

2 year growth

4%
The Tech Outlook
Apr 24th, 2025
Gladly Garners "Overall Customer Experience Solution of the Year" In 2025 RetailTech Breakthrough Awards Program

SAN FRANCISCO, April 24, 2025 (GLOBE NEWSWIRE) - RetailTech Breakthrough, a leading independent market intelligence organization that evaluates and recognizes standout retail technology companies, products, and services around the globe, today announced that Gladly, the AI-powered, people-centered Customer Service Platform, has been named "Overall Customer Experience Solution of the Year" in the 3rd annual RetailTech Breakthrough Awards program.

PR Newswire
Feb 14th, 2025
Gladly Named A Leader In Constellation Shortlist™ For Digital Customer Service And Support

Recognition Highlights the Growing Need for AI-Driven, Customer-Centered Service SolutionsSAN FRANCISCO, Feb. 14, 2025 /PRNewswire/ -- As businesses grapple with evolving customer expectations and the rapid advancement of AI, the need for customer service solutions that are both intelligent and deeply human has never been greater. In recognition of this shift, Gladly has been named to the Constellation ShortList™ for Digital Customer Service and Support for Q1 2025, marking it as a leading solution for brands looking to modernize service operations and elevate customer experiences.Constellation Research evaluates vendors based on client inquiries, market share, customer references, and independent analysis. The ShortList identifies leading solutions that help organizations modernize their technology stack and maximize the value of their investments. Gladly's inclusion reflects its innovative, customer-first model.Unlike traditional ticket-based platforms that bolt AI onto legacy workflows, Gladly was designed from the ground up to unify conversations across channels, putting customers — not tickets — at the heart of every interaction. This approach empowers brands to create seamless, personalized service experiences while simultaneously driving efficiency."Standalone AI products are simply extending legacy ticket-based customer service tools to make customers feel even more deflected," said Charlie Besecker, President of Gladly

PR Newswire
Sep 26th, 2024
Gladly secures $40M in funding led by AXA Venture Partners (AVP) and launches AI-powered unified customer service platform, transforming support into a revenue driver

/PRNewswire/ -- Gladly, a leader in customer service innovation, has announced its groundbreaking unified Customer Service Platform, powered by advanced AI....

AllBlogThings
Sep 26th, 2024
Gladly Secures $40M in Funding

In a move set to shake up the customer service industry, Gladly has launched a new AI-powered platform aimed at replacing those pesky, outdated ticket-based systems Allblogthings all know (and let's be honest, not love).

Multichannel Merchant
Jul 13th, 2023
Gladly introduces its AI and automation Customer service platform, Gladly Sidekick

Gladly Sidekick is a result of Gladly’s acquisition of Thankful, a generative AI and no-code automation solution.

INACTIVE