Deal Commercial Strategy & Operations Lead

Posted Yesterday
Be an Early Applicant
Hiring Remotely in Canada
Remote
48K-162K Annually
Senior level
HR Tech
Remote is the simple, secure platform to find, hire, manage, and pay talent anywhere, seamlessly and compliantly.
The Role
Lead the Deal Desk as a senior individual contributor: manage escalations, enforce pricing and contract compliance, build automation and playbooks, partner with Legal and Finance, track performance metrics, and drive process and tooling improvements to support high-volume enterprise deals and month/quarter close.
Summary Generated by Built In
About Remote
Remote is solving modern organizations’ biggest challenge – navigating global employment compliantly with ease. We make it possible for businesses of all sizes to recruit, pay, and manage international teams. With our core values at heart and future focused work culture, our team works tirelessly on ambitious problems, asynchronously, around the world. You can find Remoters working from 6 different continents (Antarctica left to go!) and all of our positions are fully remote.
With Innovation as one of the core values, we have built Automation and AI capabilities into the requirements for every role.
We encourage every member of the Remote team to bring their talents, experiences and culture to the table to help us build the best-in-class HR platform.
 
If you are energetic, curious, motivated and ambitious, be part of our world. Apply now and define the future of work!
What this job can offer you
  • A senior IC role with real strategic influence — you'll work directly with the Senior Manager to shape how the Deal Desk operates and evolves
  • The opportunity to lead cross-functional initiatives and drive meaningful process improvements across the Sales organization
  • A clear path towards people management as the team matures
  • A truly async, flexible work environment where ownership and proactivity are valued over process for its own sake
What you bring
  • 5+ years of experience in Deal Desk, Sales Operations, Revenue Operations, or a related function in an Enterprise SaaS/B2B company required; previous Lead or Supervisor experience is a plus
  • A proven deal desk operator with a track record of handling complex, high-stakes situations across deal structure, pricing, and contract exceptions
  • Strong understanding of Quote-to-Cash processes, revenue recognition principles, and order management
  • Deep hands-on knowledge of Salesforce (SFDC) and CPQ systems, including troubleshooting and workflow optimization
  • Natural relationship builder with the ability to engage, influence, and collaborate effectively with senior stakeholders across Go-to-Market, Legal, and Finance
  • Data-driven and analytically sharp — you turn deal trends and operational signals into clear recommendations, not just observations
  • Excellent communicator with outstanding written and spoken English
  • Calm under pressure with strong prioritization instincts, able to keep the team unblocked during high-volume periods without dropping quality
  • Self-starter who thrives in a fast-paced, fully remote, and globally distributed environment
  • Demonstrates strong automation and AI capabilities
  • It's not required to have experience working remotely, but considered a plus
Key Responsibilities
  • Act as the team's operational leader and the Senior Manager's closest extension — the go-to for escalations, the standard-setter for quality, and the primary mentor for Associates and Specialists
  • Represent the Senior Manager in cross-functional forums with Sales VPs and Sales Leadership — aligning on Deal Desk priorities and surfacing team needs and blockers
  • Serve as a senior point of contact and escalation for complex deals, non-standard pricing requests, and contract exceptions
  • Oversee deal approval processes and pricing compliance, stepping in on escalations and exceptions that require senior judgment
  • Ensure the team maintains SLA standards, stepping in to unblock or resolve complex or time-sensitive cases as needed
  • Act as the eyes and ears of the Sales team — proactively identifying deal friction, recurring blockers, and emerging risks before they escalate
  • Own the working relationship with Legal and Finance on behalf of the Senior Manager — aligning on policy, setting expectations, and ensuring the team has the guidance needed to handle non-standard situations independently
  • Develop and maintain deal playbooks and sales enablement resources, ensuring the Sales team has the guidance they need before they need to ask
  • Build and scale automated workflows that reduce manual effort and allow the team to focus on higher-value work
  • Track Deal Desk performance metrics and deal trends, translating data into actionable recommendations and feeding directly into the Senior Manager's planning and prioritisation
  • Act as the Senior Manager's operational extension — driving the Deal Desk improvement roadmap across processes, tooling, automation, and policy, and leading initiatives through to execution
  • Support month-end and quarter-end close operations to ensure smooth and accurate deal execution
Practicals
  • You'll report to: Senior Manager, Deal Commercial Strategy & Operations
  • Team: Revenue Operations — Sales Operations
  • Location: For this position we welcome everyone to apply, but we will prioritise applications from EMEA and AMER as we encourage our teams to diversify
  • Start date: As soon as possible
Application process

Roughly 6 hours across 3 weeks

  1. Interview with recruiter - 30 min
  2. Interview with Senior Manager, Deal Commercial Strategy and Operations - 45 min
  3. Interview with a cross-functional partner - 30 min
  4. (async) Deal Desk case study
  5. Case study presentation to Director, Pricing & GTM Finance and Senior Manager, Deal Commercial Strategy and Operations - 45 min
  6. Bar raiser interview - 30 min
  7. Prior employment verification check

#LI_DNP

Remote's Total Rewards philosophy is to ensure fair, unbiased compensation and fair equity pay along with competitive benefits in all locations in which we operate. We do not agree to or encourage cheap-labor practices and therefore we ensure to pay above in-location rates. We hope to inspire other companies to support global talent-hiring and bring local wealth to developing countries.

At first glance our salary bands seem quite wide - here is some context. At Remote we have international operations and a globally distributed workforce.  We use geo ranges to consider geographic pay differentials as part of our global compensation strategy to remain competitive in various markets while we hiring globally.
Our salary ranges are determined by role, level and location, and our job titles may span more than one career level. The actual base pay for the successful candidate in this role is dependent upon many factors such as location, transferable or job-related skills, work experience, relevant training, business needs, and market demands. The base salary range may be subject to change.
At Remote, we foster internal mobility as a key element of our culture of employee growth and development, supported by a compensation philosophy that guarantees pay equity and fairness. Therefore, all compensation changes associated with an internal move will be reviewed by the Total Rewards & People Enablement team on a case by case basis.

The annual salary range for this full-time position is
$48,000$162,000 USD
Benefits
Our full benefits & perks are explained in our handbook at remote.com/r/benefits. As a global company, each country works differently, but some benefits/perks are for all Remoters:
  • work from anywhere
  • flexible paid time off
  • flexible working hours (we are async)
  • 16 weeks paid parental leave
  • mental health support services
  • stock options
  • learning budget
  • home office budget & IT equipment
  • budget for local in-person social events or co-working spaces
How you’ll plan your day (and life)

We work async at Remote which means you can plan your schedule around your life (and not around meetings). Read more at remote.com/async.

You will be empowered to take ownership and be proactive. When in doubt you will default to action instead of waiting. Your life-work balance is important and you will be encouraged to put yourself and your family first, and fit work around your needs.

If that sounds like something you want, apply now!

How to apply
  1. Please fill out the form below and upload your CV with a PDF format.
  2. We kindly ask you to submit your application and CV in English, as this is the standardised language we use here at Remote.
  3. If you don’t have an up to date CV but you are still interested in talking to us, please feel free to add a copy of your LinkedIn profile instead.

Not only do we encourage folks from all ethnic groups, genders, sexuality, age, abilities, disability status and any other under-represented group to apply, but we prioritize a sense of belonging. We have 4 ERGs (Women, Disability, Queer, Minorities in Tech) who meet regularly with the People team. During your interviews and beyond, we ask & encourage anybody who needs an accommodation to request one from their recruiter.

We will ask you to voluntarily tell us your pronouns at interview stage, and you will have the option to answer our anonymous demographic questionnaire when you apply below. As an equal employment opportunity employer it’s important to us that our workforce reflects people of all backgrounds, identities, and experiences and this data will help us to stay accountable. We thank you for providing this data, if you chose to.

At Remote, we embrace AI as a valuable tool while prioritizing human creativity and authenticity. We look forward to meeting candidates who balance innovation with genuine expertise and experience. To learn more about Remote's AI guidelines check see here. 
Please note we accept applications on an ongoing basis. 

Skills Required

  • 5+ years experience in Deal Desk, Sales Operations, Revenue Operations, or related function in an Enterprise SaaS/B2B company
  • Proven track record handling complex deals, deal structure, pricing, and contract exceptions
  • Strong understanding of Quote-to-Cash processes, revenue recognition principles, and order management
  • Deep hands-on knowledge of Salesforce (SFDC) and CPQ systems, including troubleshooting and workflow optimization
  • Ability to build and scale automated workflows and demonstrate strong automation and AI capabilities
  • Data-driven with strong analytical skills to translate deal trends into recommendations
  • Excellent written and spoken English communication skills and strong stakeholder management
  • Calm under pressure with strong prioritization instincts to maintain SLA standards during high-volume periods
  • Experience engaging and influencing senior stakeholders across Go-to-Market, Legal, and Finance
  • Previous Lead or Supervisor experience
  • Prior remote work experience

Remote (Remote.com) Compensation & Benefits Highlights

The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about Remote (Remote.com) and has not been reviewed or approved by Remote (Remote.com).

  • Fair & Transparent Compensation Pay is positioned as above-market with a stated 65th-percentile benchmarking approach and structured bands/compa-ratios for adjustments. Compensation equity checks (including role and gender fairness) and inclusion of statutory local allowances are described as part of the approach.
  • Leave & Time Off Breadth Time-off offerings are described as expansive, including unlimited PTO with a stated minimum, local public holidays, and periodic company-wide self-care days. Asynchronous hours and flexible scheduling are also highlighted as part of the time-off and flexibility experience.
  • Wellbeing & Lifestyle Benefits Benefits include home office support and equipment, wellness programs, mental-health support, and allowances for learning and professional development. Additional perks like meetups/workations and recognition-style perks are described as part of the total package.

Remote (Remote.com) Insights

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The Company
HQ: San Francisco, CA
1,004 Employees
Year Founded: 2019

What We Do

Talent is everywhere. Opportunity is not. Remote's mission is to create opportunity everywhere, empowering employers to find and hire the best talent, and enabling individuals to build financial and personal freedom. Remote is the all-in-one HR and payroll platform to find, hire, manage, and pay your entire team everywhere. Whether onboarding your first cross-border hire or scaling across continents, Remote delivers enterprise-grade compliance, intuitive design, and dedicated local expertise. With one platform for every contract, payslip, and regulation, Remote helps you grow without borders through our comprehensive set of core solutions including, HRIS, payroll, international employment, contractor management, and more.

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