Deal Desk Specialist - Remote (Ontario)

About Highspot

Highspot is pioneering the category that is fundamentally changing the way companies increase sales productivity. On a mission to transform the way millions of people work with sales enablement, Highspot is committed to building breakthrough software with a spark of magic. We believe a great place to work is about more than the work – it’s about what the company stands for, and how it authentically represents its values in the real world. To this end, we have put intentional focus on creating equitable workspaces for each of our employees. Our goal is to create a culture where everyone feels a deep sense of belonging and is empowered to be an agent of change, with the ability to transform themselves, their workplace, and their world.

About the Role 

Highspot is seeking a Deal Desk Specialist to join our growing team. In this role, you will be the key enabler for our sales team, streamlining the contracting processes and ensuring optimal deal structuring for customer contracts. You will collaborate with account executives, account managers, customer success managers, legal, and accounting teams to ensure renewals are processed efficiently, driving revenue growth and maximizing retention.

We are growing fast and are looking for individuals to build a world-class experience for our sales team. The person we are looking for has strong communication and organizational influence skills, and can acknowledge and balance the different needs of all relevant stakeholders. They are able to partner closely with various leaders to help drive strategy and behaviors that support the renewals motion.

What You'll Do

• Provide strategic guidance on pricing, discounting, and deal terms for new business, expansions & renewals, helping teams create proposals that align with business goals while maintaining customer satisfaction.
• Assist Account Executives & Account Managers in structuring and executing deals, ensuring alignment with company policies, pricing guidelines, and customer needs.
• Partner with accounting, legal, and revenue operations teams to ensure all agreements are compliant, accurately structured, and financially sound.
• Develop and refine deal desk processes to enhance efficiency, transparency, and ease of execution for our sales teams.
• Monitor and report on key metrics such as renewal rates, pricing trends, and discount levels. Provide actionable insights to drive improvements in the renewal process.
• Educate and train sales and customer success teams on renewal best practices, deal desk processes, and how to effectively position pricing strategies during the renewal phase.
• Manage and track the approval process for complex or high-value deals, ensuring appropriate internal approvals are obtained in a timely manner.

Your Background

• 2+ years of experience in operations, strategy, or deal desk within a SaaS company. 
• Strong negotiation, communication, and interpersonal skills. Ability to present and discuss contract terms with confidence and clarity.
• Experience partnering with different go-to-market teams, ideally, pre & post-sales.
• Ability to cover a range of activities; from presentations to hands-on, process improvement with Revenue Operations team members.
• A very thorough understanding of licensing models, pricing structures and customer contracts.
• Strong communication skills, including the ability to summarize and visualize complex Customer situations. 
• Excellent organizational skills with the ability to manage multiple processes simultaneously while ensuring accuracy in all aspects of customer communication and contract management.
• Salesforce experience preferred 

This position is available either in-office or remote, as applicable, at the following locations:

• Ontario - Remote

Base salary range: $71,000 - $106,000 CAD. Employees are eligible to receive stock options and may also receive other forms of compensation.

The above represents total expected compensation for this role. Actual compensation will depend on various job-related factors, including, but not limited to, location, experience, and job qualifications.

Highspot also offers the following employee benefits for this position:

-Comprehensive medical, dental, vision, disability, and life benefits

-Group Retirement Savings Plan (RRSP) and matching employer contributions (DPSP) with immediate vesting

-Flexible PTO

-Generous Holiday Schedule + 5 Days for Annual Holiday Week

-Quarterly Recharge Fridays (paid days off for mental health recharge)

-Flexible work schedules

-Access to Coaches and Therapists through Modern Health

-2 Volunteer days per year

-Monthly transportation allowance for employees that work in our Vancouver Hub location

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Equal Opportunity Statement

We are an equal opportunity employer and value diversity at our company. We do not discriminate on the basis of any grounds protected by applicable human rights legislation, which may include age, ancestry, citizenship, color, ethnicity, family status, gender identity or expression, genetic information, marital status, medical condition, national origin, physical or invisible disabilities, political belief, race, religion, or sexual orientation.

Did you read the requirements as a checklist and not tick every box? Don't rule yourself out! If this role resonates with you, hit the ‘apply’ button."