Deal Desk Analyst, Gladly
$85-100k
OTE
+ Equity
Customer experience AI built for LTV
Be an early applicant
Customer experience AI built for LTV
201-500 employees
Be an early applicant
$85-100k
OTE
+ Equity
201-500 employees
Company mission
To make customer service radically personal.
Role
Who you are
- 2-4 years of experience in deal desk, commercial finance, revenue operations, sales operations, or a related operational finance role. B2B SaaS experience is a plus but not required
- Based in the US with the ability to work standard US business hours
- Exposure to deal desk or quote-to-cash processes: you have some familiarity with deal review, pricing compliance, approval workflows, or commercial operations even if you have not owned the full function
- Salesforce experience: comfortable navigating the platform and working with deal data. Admin-level experience is a plus
- Familiarity with SaaS business model fundamentals: ARR, ACV, and how subscription revenue works. You do not need to be an expert, but you should understand the basics
- Comfortable with spreadsheets: Google Sheets or Excel at an intermediate-to-advanced level (formulas, pivot tables, data analysis)
- Strong attention to detail and follow-through. You notice when something is off and you do not let it slide
- A bias toward action and execution. You do not need to be told what to do next, you figure it out
- Collaborative and communicative: you over-communicate, you ask good questions, and you are comfortable working across teams
- DealHub, CPQ, or deal desk systems experience is a strong differentiator
- Research has shown that individuals from underrepresented groups are less likely to apply to jobs where they don't meet 100% of the criteria. Gladly values diversity of experience. If you believe you have the right skill set, we welcome you to apply even if you don't check every box. We are committed to an inclusive workplace and would love to see if you could be the next great addition to our team
What the job involves
- This role puts you at the center of deal desk operations and commercial finance at a company redefining customer experience through agentic AI
- You will start by working alongside experienced Finance and Systems teammates to build fluency in how deals get structured, priced, and closed, and you will move quickly toward ownership of the quote-to-cash workflow
- This is not a back-seat role
- We are looking for someone who learns fast, takes initiative, and is ready to own outcomes within their first six months
- You are detail-oriented, execution-focused, and energized by operational work that has real business impact
- You do not wait to be told what to do next
- You see a gap, you close it
- You are not intimidated by ambiguity or new systems, and you bring the kind of follow-through and accountability that earns trust fast
- You may be earlier in your career, but you operate like someone who has been doing this for years
- Gladly is at the forefront of AI-powered customer experience, and our commercial motion is accelerating to match
- This role gives you direct responsibility across deal review, pricing analysis, systems configuration, and cross-functional partnership with sales
- The technology is evolving fast, the deal structures are evolving with it, and the right person in this seat will grow into a core operator on the Finance team, not stay in a support role
- Support deal reviews for completeness, accuracy, and compliance before close, working alongside senior Finance teammates to ensure deals are structured correctly across pricing, discounting, and contract terms
- Help manage the day-to-day quote-to-cash workflow in Salesforce: deal progression tracking, certification process management, renewals tracking, and pipeline reporting
- Maintain a clean approval audit trail and deal log to support accurate pipeline reporting and downstream revenue recognition
- Learn and apply pricing compliance guidelines, discount thresholds, and revenue recognition requirements (ASC 606) with increasing independence over time
- Support the margin calculator used to evaluate pricing structures on enterprise deals, building comfort with how AI vs. Team margin dynamics affect deal economics
- Flag friction points in the Deal Desk process and bring ideas for improvement to the team
- Help support deal desk systems including DealHub (CPQ) and Salesforce, contributing to data integrity and process consistency under the guidance of the Systems Design team
- Assist with configuring and optimizing deal desk tooling, including approval workflows, pricing rules, and quote templates
- Help identify opportunities to automate recurring processes and reduce manual effort across the deal desk function
- Show genuine curiosity about AI tools (Claude, ChatGPT, Copilot, or similar) and a willingness to learn how they can help you move faster and reduce the lift on repetitive tasks
- Apply an automation-first lens to your own work: if you are doing something manually more than twice, start thinking about how to streamline it
- Partner with the Finance team on identifying and implementing AI-assisted workflows across Deal Desk processes
Our take
Gladly is a cloud-based platform integrating multiple customer service channels into a single UI. It helps companies cater to the upward trend in personalized service by allowing them to communicate with their customers seamlessly across any channel from voice, email, messaging, chat and social media.
The rise in eCommerce has meant demand for services like Gladly is growing. To stand out, the company has focussed on building out its platform with new features. Most lately, this has included an AI and automation-driven customer service platform.
As a certified app partner to Shopify, Gladly benefits from the ability of Shopify merchants to integrate directly with its platform. The company has raised considerable funding, the latest of which supports accelerated growth on the back of releasing its unified customer service platform.
Kirsty
Company Specialist at Welcome to the Jungle
Insights
15% employee growth in 12 months
Company
Funding (last 2 of 6 rounds)
Sep 2024
$40m
LATE VC
Dec 2022
$55m
LATE VC
Total funding: $208m
Company benefits
- Stock options
- Medical, Dental, Vision and Life insurance
- Generous paid time off
- Generous paid Parental Leave
- 401K
- Flexible Spending Accounts
- Home office stipends
Company HQ
Bernal Heights, San Francisco, CA
Leadership
Charlie Besecker
(CEO)Charlie joined Gladly in 2024 as a President, moving into the role of CEO in 2025. Prior to this, he was a CRO at GRIN and Route.
Joseph Ansanelli
(Co-Founder & Executive Chairman)After co-founding Gladly in 2015, Joseph served as the CEO until 2025. He has also been at Greylock since 2012, spending 5 years as a General Partner before becoming a Venture Partner.
Andy D'Amato
(CRO)Prior to joining Gladly in 2022, Andy spent nearly 9 years at PTC. While there he held a number of roles, including Senior VP of Sales, Americas IoT & Augmented Reality and Senior VP of Global IoT Sales.
Todd Rakow
(CFO)Todd joined Gladly in 2019 as a VP of FInance & Operations before moving into the role of CFO in 2022. Previously, he co-founded Kanjoya and served as the CFO for nearly 6 years. He also spent some time at PayPal as a Senior Operations & Strategy Manager.
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