Senior Deal Desk Analyst

Senior Analyst, Deal Desk

Achievers offers more than just a thank you program. Our employee recognition and rewards software inspires employees to recognize everyone, every day, everywhere. With 4.3 million global users, we empower employees across 190 countries. Join our team of A-players who bring passion to our purpose and believe that meaningful change creates extraordinary outcomes — together, we'll inspire recognition everywhere and achieve results that matter.

We are seeking a strategic and execution-focused Senior Analyst, Deal Desk to help evolve and mature our Deal Desk function. This is a hands-on individual contributor role that combines day-to-day deal execution with subject matter expertise and functional ownership. You will operate as both a player and a builder—owning deal desk ticket execution and complex deal support while driving process optimization, automation, and scalable improvements.

You will partner closely with Sales, Customer Success, Legal, and Finance to structure high-quality deals across land, expand, and renewal motions, directly impacting ARR growth, deal velocity, and long-term customer value. You will enable efficient deal progression while also building the frameworks, guardrails, and processes that create consistency and scale. You will balance strong collaboration and commercial flexibility with clear standards and operational rigor, ensuring deals support both immediate revenue objectives and sustainable growth, while reducing friction in the deal process by improving upfront clarity and enabling stronger deal structuring at the source.

How you'll own the Deal Desk function at Achievers:

• Own and execute day-to-day Deal Desk support, including managing deal reviews, pricing requests, discount approvals, and contract structuring across new business, expansion, and renewal deals
• Lead complex and non-standard deals, providing strategic guidance on pricing, licensing models, and commercial constructs
• Partner with Sales and Customer Success to structure competitive, scalable, and compliant deals, acting as a thought partner to drive the right deal outcomes—not simply an approval step
• Provide clear guidance and transparency on pricing, approvals, and deal structures to help Sales and Customer Success navigate trade-offs and drive more efficient deal execution
• Apply sound judgment to balance sales velocity with pricing integrity, margin protection, and long-term revenue outcomes
• Act as the primary liaison between Sales, Legal, and Finance to align on contract terms, approvals, and deal strategy
• Support commissions processes during monthly and quarterly cycles by contributing to crediting validation, exception review, and payout accuracy, stepping in during peak periods or planned absences and applying Deal Desk judgment to ensure consistent, compliant compensation outcomes.
• Serve as an escalation point for high-impact or non-standard deals, providing clear and data-driven recommendations
• Act as a subject matter expert (SME) for deal structuring, pricing strategy, and contracting best practices across the organization
• Mentor and support Deal Desk Analysts, sharing subject matter expertise and elevating team capability, consistency, and judgment
• Define and evolve pricing frameworks, discount matrices, approval governance, and deal guardrails
• Build, document, and standardize Deal Desk processes, playbooks, and operating procedures to drive consistency, clarity, and scalability
• Identify and implement opportunities for process optimization, automation, and workflow improvements to reduce manual effort and increase efficiency
• Streamline deal approval and contract workflows to accelerate deal cycle times while maintaining appropriate controls and compliance
• Develop reporting and dashboards to track deal performance, discounting trends, and operational effectiveness
• Enable Sales and Customer Success teams through training and ongoing guidance on pricing, deal structuring, tools, and processes, empowering teams to structure stronger deals upfront
• Foster a culture of continuous improvement, balancing collaboration and responsiveness with strong operational discipline, accountability, and consistency

Experience we feel will set you up for success:

• 6+ years of experience in Deal Desk, Commissions, Sales Operations, or Revenue Operations within a B2B SaaS environment
• Proven ability to operate in a high-volume, hands-on deal environment while contributing strategically as a subject matter expert
• Strong expertise in SaaS pricing models, discounting, contract structuring, and deal strategy
• Experience building, documenting, and optimizing scalable processes and workflows
• Demonstrated experience driving process improvements and automation initiatives
• Strong cross-functional collaboration experience with Sales, Customer Success, Legal, Finance, and related stakeholders
• Proficiency with Salesforce (or equivalent CRM), CLM tools, and workflow/automation systems
• Advanced Excel or Google Sheets skills with strong analytical and data interpretation capabilities
• Excellent communication and stakeholder management skills, with the ability to influence without direct authority
• Demonstrated ability to balance a collaborative, solution-oriented approach with adherence to business policies, guardrails, and operational consistency
• Strong attention to detail and ability to manage competing priorities in a fast-paced environment

Why you'll love working at Achievers:

We are passionate about disruptive technology that's rooted in science, research and data.

We understand the value of employee success in the workplace and have been recognized in numerous publications for our contributions to HR, for technical excellence, and for our outstanding workplace culture!

We foster an environment of connection, security, and community. You'll feel at home, without reservation.

We believe in moving quickly, failing fast, and adapting to change.

We enjoy coming to work every day because we believe in our product and love our culture.

We're committed to achieving excellence in everything we do.

Our work environment:

Achievers is a hybrid-first company located at 99 Atlantic Ave in Liberty Village, Toronto. Our hybrid work experience is designed to cultivate an engaging employee experience, where pioneering research intersects with cutting-edge technology. We strongly believe that collocating teams increases the chance to innovate together, foster passive learning, create spontaneous connections, and promote better communication.

Achievers does not offer employment to prospects without first ensuring that qualified candidates speak directly with the hiring manager and a member of our HR team. All qualification will be done face-to-face, whether that is in person or over Zoom. Achievers does not send out offers of employment without meeting candidates and does not offer employment via text. If you are requested for any personal information via text and/or without having met a member of our hiring team in person, please disregard.

Our employees are a diverse and inclusive team of passionate, hardworking individuals. Achievers is an equal opportunity employer, committed to creating an environment where our employees can do the best work of their lives. We encourage all qualified candidates from all backgrounds and experiences to apply to join our A-Player family.

Achievers is committed to ensuring an inclusive and accessible recruitment process for all candidates. If you require any accommodations for your interview, such as assistive technology, wheelchair accessibility, or alternative formats of materials, please let us know. We are happy to make necessary arrangements to support your needs.