Director of Enterprise Sales, IgniteTech (Remote) - $200,000/year USD at Crossover
Date: 4 hours ago
City: Toronto, ON
Contract type: Full time
Remote
Enterprise software typically fails not from a shortage of customer names, but from the quiet erosion of revenue tied to logos already secured. In long-cycle B2B environments, 70–90% of the following year's revenue depends on your ability to renew effectively, expand strategically, and rescue at-risk accounts. Forecast drift, poorly drafted SOWs, and inadequate escalation protocols erode both margin and credibility. The outcome: unmet targets, CFO doubt, and clients who view you as interchangeable rather than indispensable.
Our approach is fundamentally different. We operate a system-driven commercial engine where disciplined process outperforms individual heroics. We generate profitable, enduring revenue from an established Fortune-level customer base via clean renewals, targeted expansions, and executive-level escalation management. Commercial structure is treated as a core product: margin-protecting proposals, delivery-enabling contracts, and QBRs that genuinely advance adoption.
This position is not a role offering autonomy without structure, nor is it a place for those relying on optics or inflated pipeline metrics. It suits someone energized by forecast precision, margin-safe deal architecture, tightly drafted SOWs, and executive dialogues that conclude with clarity and commitment. You'll apply genuine GenAI expertise to accelerate analysis and communication, exercise sound commercial judgment in uncertain situations, manage escalations with composure, and coach the team to refine pricing, structure, and negotiation. If you've directed enterprise B2B software sales with accountability for renewals, expansions, multi-year agreements, SLAs, and pricing frameworks, you'll recognize this environment.
If you're presently leading or have recently overseen an enterprise sales organization in SaaS, or you've advanced through senior positions such as Sales Director, Regional VP, or Head of Enterprise Accounts following an early career grounded in rigorous pipeline discipline, let's connect. Enter a role where your expertise isn't compromised by disorder, and take ownership of the engine that truly defines next year's performance. Apply if you're prepared to demonstrate that structured commercial execution consistently outperforms optimism.
What You Will Be Doing
World-class talent. 100% global remote.
Ready to be a part of the top talent that IgniteTech has curated from thousands of applicants throughout the world? Come join us.
Through our portfolio of leading enterprise software solutions, we ignite business performance for thousands of customers globally. We’re big believers in the remote-work-from-anywhere lifestyle, which creates freedom for our team members and enables us to hire the best and brightest from around the world. A career with IgniteTech is challenging and fast-paced and we’re always looking for energetic and enthusiastic team members.
We’re an Affirmative Action and Equal Opportunity employer and we value the strength that diversity brings to our workplace.
There is so much to cover for this exciting role, and space here is limited. Hit the Apply button if you found this interesting and want to learn more. We look forward to meeting you!
Working with us
This is a full-time (40 hours per week), long-term position. The position is immediately available and requires entering into an independent contractor agreement with Crossover as a Contractor of Record. The compensation level for this role is $100 USD/hour, which equates to $200,000 USD/year assuming 40 hours per week and 50 weeks per year. The payment period is weekly. Consult www.crossover.com/help-and-faqs for more details on this topic.
Crossover Job Code: LJ-5695-CA-Toronto-DirectorofEnte
Our approach is fundamentally different. We operate a system-driven commercial engine where disciplined process outperforms individual heroics. We generate profitable, enduring revenue from an established Fortune-level customer base via clean renewals, targeted expansions, and executive-level escalation management. Commercial structure is treated as a core product: margin-protecting proposals, delivery-enabling contracts, and QBRs that genuinely advance adoption.
This position is not a role offering autonomy without structure, nor is it a place for those relying on optics or inflated pipeline metrics. It suits someone energized by forecast precision, margin-safe deal architecture, tightly drafted SOWs, and executive dialogues that conclude with clarity and commitment. You'll apply genuine GenAI expertise to accelerate analysis and communication, exercise sound commercial judgment in uncertain situations, manage escalations with composure, and coach the team to refine pricing, structure, and negotiation. If you've directed enterprise B2B software sales with accountability for renewals, expansions, multi-year agreements, SLAs, and pricing frameworks, you'll recognize this environment.
If you're presently leading or have recently overseen an enterprise sales organization in SaaS, or you've advanced through senior positions such as Sales Director, Regional VP, or Head of Enterprise Accounts following an early career grounded in rigorous pipeline discipline, let's connect. Enter a role where your expertise isn't compromised by disorder, and take ownership of the engine that truly defines next year's performance. Apply if you're prepared to demonstrate that structured commercial execution consistently outperforms optimism.
What You Will Be Doing
- Steering renewals and expansions from pipeline development through final signature
- Conducting executive reviews and overseeing escalation management
- Designing and authorizing commercial proposals and contracts engineered to withstand scrutiny
- Grow enterprise account revenue and retention via disciplined commercial execution, strategic account stewardship, and seamless customer integration
- A minimum of 10 years of experience in the IT industry and 5 years of experience in the B2B enterprise software sector
- A minimum of 5 years of experience managing renewals, expansions, or account growth initiatives
- Demonstrated experience leveraging LLMs and other GenAI tools to optimize workflows
- Proven experience managing multi-million-dollar enterprise accounts
- Hands-on experience with CRM systems and Order-to-Cash (O2C) processes
- Background working with regulated industry customers (finance, healthcare, or pharma), including compliance-driven commercial frameworks
- Experience leading sales or account management teams in quota-carrying capacities and coaching on deal structure and negotiation tactics
World-class talent. 100% global remote.
Ready to be a part of the top talent that IgniteTech has curated from thousands of applicants throughout the world? Come join us.
Through our portfolio of leading enterprise software solutions, we ignite business performance for thousands of customers globally. We’re big believers in the remote-work-from-anywhere lifestyle, which creates freedom for our team members and enables us to hire the best and brightest from around the world. A career with IgniteTech is challenging and fast-paced and we’re always looking for energetic and enthusiastic team members.
We’re an Affirmative Action and Equal Opportunity employer and we value the strength that diversity brings to our workplace.
There is so much to cover for this exciting role, and space here is limited. Hit the Apply button if you found this interesting and want to learn more. We look forward to meeting you!
Working with us
This is a full-time (40 hours per week), long-term position. The position is immediately available and requires entering into an independent contractor agreement with Crossover as a Contractor of Record. The compensation level for this role is $100 USD/hour, which equates to $200,000 USD/year assuming 40 hours per week and 50 weeks per year. The payment period is weekly. Consult www.crossover.com/help-and-faqs for more details on this topic.
Crossover Job Code: LJ-5695-CA-Toronto-DirectorofEnte
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