Deal Desk Analyst



Sterling, VA, USA
Posted on Tuesday, October 17, 2023

Grammarly is excited to offer a remote-first hybrid working model. Team members work primarily remotely in the United States, Canada, Ukraine, Germany, or Poland. Certain roles have specific location requirements to facilitate collaboration at a particular Grammarly hub.

All roles have an in-person component: Conditions permitting, teams meet 2–4 weeks every quarter at one of Grammarly’s hubs in San Francisco, Kyiv, New York, Vancouver, and Berlin, or in a workspace in Kraków. This flexible approach gives team members the best of both worlds: plenty of focus time along with in-person collaboration that fosters trust and unlocks creativity.

Grammarly team members in this role must be based in the United States or Canada, and they must be able to collaborate in person 2 weeks per quarter, traveling if necessary to the hub(s) where the team is based.

The opportunity

Every day, tens of millions of people and 50,000 professional teams worldwide trust Grammarly’s AI and human expertise to help ideate, compose, revise, and comprehend communications. Our team members have the autonomy to take on exciting challenges in pursuit of our mission to improve lives by improving communication. Together, we’re building on more than a decade of steady growth and profitability. We’re defining the communication assistance category with our tailored service offerings: Grammarly Free, Grammarly Premium, Grammarly Business, and Grammarly for Education. Our latest product offering, GrammarlyGO, brings the power of generative AI to our users. It all begins with our team collaborating in an inclusive, values-driven, and learning-oriented environment.

To achieve our ambitious goals, we’re looking for a Deal Desk Analyst to join our Revenue Operations team. The Deal Desk Analyst will be a core part of our Sales Operations team, working closely with AEs and CSMs to close revenue and maximize value. The person in this role will ensure smooth deal desk operations, review complex deals and pricing strategies, and conduct deal reviews for both Grammarly Business and Grammarly for Education.

Your impact

As a Deal Desk Analyst, you will collaborate with the Sales and Finance team to drive a strategic partnership to close new business, build expansion deals, and foster customer retention and growth. In this role, you’ll work effectively with business partners, addressing complex challenges to achieve the overall function's success. You can focus entirely on the deal desk craft, taking the initiative to help with enterprise deals and incorporate best practices into processes. In this position, you’ll be held to a high standard of excellence and operate with a sense of urgency, detail orientation, and strategic mindset while regularly taking a step back to think about the big picture.

Within your first 30 days, you will:

  • Complete general onboarding and meet the team.
  • Familiarize yourself with the complete Grammarly sales process from start to finish, making it part of your knowledge base.
  • Delve into the deals and review the seller's experience to understand the sales process better.
  • Develop relationships with key partners in sales, operations, and finance.
  • Create a 30-day retrospective report outlining key learnings and explore growth opportunities.

Within three months, you will:

  • Understand customer requirements to provide swift sales feedback for pricing, deal structure, and applicable terms.
  • Manage complex contracts and deal strategies in a high-growth SaaS environment.
  • Identify and evaluate non-standard opportunities and conduct practical deal review sessions with Sales Reps to make progress on deals.
  • Collaborate closely with representatives from all teams to identify new business opportunities and drive expansion bookings through effective deal segmentation and reporting.

Within six months, you will:

  • Deeply understand trends in pricing, opportunities, and behavior to positively influence the back-of-funnel sales process.
  • Ensure compliance with business processes and policies while fostering strong cross-functional alignment between the sales, finance, and revenue operations teams.
  • Deliver sales training on core deal desk processes to promote scale and sales productivity.
  • Leverage data insights to drive decision-making and streamlined processes with business growth and scale in mind.

Within twelve months, you will:

  • Reduce process inefficiencies and identify opportunities to strengthen the quote-to-cash workflow and reduce cycle time.
  • Regularly participate in key deals alongside stakeholders and provide expertise as a subject matter expert for the deal desk.
  • Analyze nonstandard deals to optimize their structure and make recommendations.
  • Improve measurable KPIs such as deal size, volume, and efficiency to impact our Quote to Cash deal flow positively.

We’re looking for someone who

  • Embodies our EAGER values—is ethical, adaptable, gritty, empathetic, and remarkable.
  • Is able to collaborate in person 2 weeks per quarter, traveling if necessary to the hub where the team is based.
  • Is inspired by our MOVE principles, which are the blueprint for how things get done at Grammarly: move fast and learn faster, obsess about creating customer value, value impact over activity, and embrace healthy disagreement rooted in trust.
  • Seeks to become a trusted advisor to sales and customer success reps and has a track record of building solid relationships.
  • Takes extreme ownership of their work and has experience balancing tactical and strategic work in a Deal desk function.
  • Is naturally inclined to make decisions that benefit the business while being comfortable working independently and as a team player to solve problems.
  • Is an effective collaborator and excellent interpersonal skills.
  • Has strong written and verbal communication skills.
  • Has salesforce experience with the ability to build basic reports and dashboards.
  • Is proficient with CPQ tools, DealHub.
  • Has a proven ability to structure deals successfully and manage deal flow with varying constructs, such as currency, terms length, and deal type.
  • Has 4-5 years experience in Deal Desk in a high-growth SaaS environment.
  • Has B2B SaaS experience in Ops or Sales roles of varying company size.
  • Has a strong understanding of B2B quote to cash processes and general deal segmentation strategies.

Support for you, professionally and personally

  • Professional growth: We believe that autonomy and trust are key to empowering our team members to do their best, most innovative work in a way that aligns with their interests, talents, and well-being. We support professional development and advancement with training, coaching, and regular feedback.
  • A connected team: Grammarly builds a product that helps people connect, and we apply this mindset to our own team. Our remote-first hybrid model enables a highly collaborative culture supported by our EAGER (ethical, adaptable, gritty, empathetic, and remarkable) values. We work to foster belonging among team members in a variety of ways. This includes our employee resource groups, Grammarly Circles, which promote connection among those with shared identities, such as BIPOC and LGBTQIA+ team members, women, and parents. We also celebrate our colleagues and accomplishments with global, local, and team-specific programs.

Compensation and benefits

Grammarly offers all team members competitive pay along with a benefits package encompassing the following and more:

  • Excellent health care (including a wide range of medical, dental, vision, mental health, and fertility benefits)
  • Disability and life insurance options
  • 401(k) and RRSP matching
  • Paid parental leave
  • Twenty days of paid time off per year, eleven days of paid holidays per year, and unlimited sick days
  • Home office stipends
  • Caregiver and pet care stipends
  • Wellness stipends
  • Admission discounts
  • Learning and development opportunities

Grammarly takes a market-based approach to compensation, which means base pay may vary depending on your location. Our US and Canada locations are categorized into compensation zones based on each geographic region’s cost of labor index. For more information about our compensation zones and locations where we currently support employment, please refer to this page. If a location of interest is not listed, please speak with a recruiter for additional information.

Base pay may vary considerably depending on job-related knowledge, skills, and experience. The expected salary ranges for this position are outlined below by compensation zone and may be modified in the future.

United States:
Zone 1: $122,000 - $153,000/year (USD)
Zone 2: $110,000 - $138,000/year (USD)
Zone 3: $103,000 - $130,000/year (USD)
Zone 4: $98,000 - $122,000/year (USD)
Zone 1: $92,000 - $113,000/year (CAD)
Zone 2: $78,000 - $97,000/year (CAD)

We encourage you to apply

At Grammarly, we value our differences, and we encourage all—especially those whose identities are traditionally underrepresented in tech organizations—to apply. We do not discriminate on the basis of race, religion, color, gender expression or identity, sexual orientation, ancestry, national origin, citizenship, age, marital status, veteran status, disability status, political belief, or any other characteristic protected by law. Grammarly is an equal opportunity employer and a participant in the US federal E-Verify program (US). We also abide by the Employment Equity Act (Canada).

Please note that EEOC is optional and specific to US-based candidates.




All team members meeting in person for official Grammarly business or working from a hub location are strongly encouraged to be vaccinated against COVID-19.