Senior Deal Desk Analyst

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,, 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.

Please note that this opportunity is a 12 month contract.

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 complian 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 Achievers is a Great Place to Work™

At Achievers, we believe recognition is a powerful driver of connection. With more than 4.3 million users across 190 countries, our employee recognition and rewards platform empowers organizations to build cultures where people feel seen and valued, everyday. We’re a team of passionate, thoughtful builders who care deeply about our product, our customers, and each other. Visit achievers.com to see how we’re inspiring recognition everywhere.

Our Approach to Total Rewards

We’re committed to providing a fair and competitive offer based on what you bring to the team. Each A-Players' compensation is reviewed at least annually against performance and impact in role. We want you to see your path to growth, understand your impact, and feel valued every step of the way.

$94,000 - $115,000 reflects what we reasonably expect to offer for this role based on current market data. The final offer will depend on several factors, including your skills, experience, and any relevant certifications. As with all market-based ranges, these numbers may evolve over time, but we’re committed to providing a fair and competitive offer based on what you bring to the team.

Benefits and Perks for permanent full-time employees:

✨ Rewards for your impact through our Recognition and Rewards program

Employee and Family Assistance Program offering mental health, legal, and financial counselling

Supported professional development and career growth (Linkedin Learning, mentorship)

Employee-Led Employee Resource Groups that celebrate our diversity

️ Regular events designed to build connection, belonging, and well-being

Hybrid flexibility, with time in our beautiful Liberty Village, Toronto office

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.

We may use artificial intelligence (AI) tools to support parts of our hiring process, such as reviewing applications or analyzing resumes. These tools help our recruitment team but never replace decisions made by real people. We believe in a human-first approach to hiring, where your experience, personality, and potential are recognized by people, not algorithms, and where final hiring decisions are made by humans. If you would like more information about how your data is processed, please contact us.