How Opal Security Structures Compensation to Drive Strategic Account Focus

How Opal Security Structures Compensation to Drive Strategic Account Focus

Sales teams are economic actors. They optimize for whatever generates the highest personal return. Tell them to focus on enterprise accounts while paying them the same commission for $50,000 mid-market deals and $500,000 enterprise deals, and they’ll rationally choose the path of least resistance. The faster close always wins when compensation is neutral to deal size. In a recent episode of Category Visionaries, Umaimah Khan, CEO and Co-Founder of Opal Security, shared how her team restructured compensation to align sales behavior with strategic priorities—shifting focus from volume-based mid-market sales to strategic enterprise accounts that drove sustainable growth.

The insight wasn’t complicated. The execution required precision.

The Misalignment Between Strategy and Incentives

Opal’s product-led growth motion generated strong mid-market traction. Engineers discovered the product, adopted it for their teams, and expanded usage organically. Sales reps could close these deals relatively quickly—30 to 60 day cycles, minimal executive involvement, straightforward procurement processes.

Enterprise deals were different. They required months of relationship building, complex stakeholder management, and extensive sales engineering support. Multiple decision-makers. Security reviews. Legal negotiations. Executive sponsorship. The same sales rep effort that closed three mid-market deals might only close one enterprise deal in the same timeframe.

As long as compensation treated all deals equally, sales teams naturally gravitated toward mid-market. Why spend six months navigating a Fortune 500 procurement process when you could hit quota through accumulated smaller wins? The rational economic decision was optimizing for volume, even when company strategy demanded enterprise focus.

“We structured our sales comp to reward larger deals with better margins,” Umaimah notes. “We wanted our team focused on enterprise accounts, not churning through small deals.” This wasn’t about paying sales teams more money—it was about changing the relative economics to make enterprise pursuit the rational choice.

The Economics of Deal Size Prioritization

The compensation restructuring created meaningful financial incentives for pursuing larger deals. Enterprise accounts received higher commission rates, accelerators for deals above certain thresholds, and bonus structures tied to strategic account metrics rather than just closed revenue.

The math shifted. A sales rep closing a $500,000 enterprise deal now earned significantly more than closing ten $50,000 mid-market deals—even accounting for the longer sales cycle and higher effort. The commission differential needed to be substantial enough to overcome the psychological preference for frequent, smaller wins.

But incentive changes alone weren’t sufficient. Opal also needed to ensure sales teams had the tools and support to actually win enterprise deals. “We had to professionalize everything,” Umaimah says. “Hire experienced enterprise AEs, build out sales engineering, create proper deal review processes, implement Salesforce correctly—all the blocking and tackling of enterprise sales.”

The compensation change and infrastructure investment worked in tandem. Higher commissions incentivized enterprise pursuit. Better enablement made enterprise pursuit viable. Without both elements, the strategy would fail—either through misaligned incentives or impossible execution.

Beyond Commission Rates: Strategic Account Metrics

Commission structure was only one component of the compensation redesign. Opal also introduced metrics that rewarded behaviors beyond just closed revenue. Strategic account engagement, executive relationship building, multi-year contract terms, and expansion potential all factored into compensation calculations.

This mattered because enterprise sales requires different activities than mid-market transactional sales. In mid-market, volume is everything—more demos, more proposals, more closes. In enterprise, relationship depth is critical. A sales rep might spend weeks building executive relationships before any formal opportunity exists.

Traditional sales compensation focused purely on closed deals penalizes this necessary enterprise behavior. Why invest time in relationship building when you could be closing transactional deals? Opal’s compensation structure needed to value strategic activities that might not immediately generate revenue but created pipeline for larger future opportunities.

The shift changed sales team behavior. Reps started investing more time with strategic accounts. They built relationships with CISOs and CFOs, not just engineering managers. They pursued multi-year commitments instead of annual contracts. The economic incentives made long-term strategic thinking personally profitable.

Managing the Transition Period

Changing compensation structures mid-flight is operationally complex. Existing sales reps have expectations based on current plans. Quota attainment calculations change. Territory assignments might need restructuring. The transition period requires careful management to avoid destroying team morale or losing productive reps.

Opal managed this by grandfathering certain elements for existing team members while implementing new structures for new hires. This created temporary comp complexity but avoided the disruption of forcing immediate changes on the entire team.

The transition also required clear communication about strategic direction. Sales teams needed to understand why compensation was changing and how the new structure aligned with company priorities. “We wanted our team focused on enterprise accounts, not churning through small deals,” Umaimah explains. Transparency about the strategic shift helped teams understand that compensation changes weren’t arbitrary—they reflected genuine business priorities.

The Broader Sales Infrastructure Changes

Compensation restructuring was effective because it happened alongside broader sales infrastructure improvements. “We created detailed battle cards, competitive positioning documents, ROI calculators, reference architectures,” Umaimah explains. “Our sales team needed to handle objections about budget, timing, competitive alternatives, and technical requirements—often all in the same deal.”

These enablement materials served dual purposes. They made enterprise selling operationally feasible, and they signaled organizational commitment to enterprise strategy. Sales teams could see the company was investing in their success with strategic accounts, not just demanding different behavior without providing support.

The infrastructure investment included hiring experienced enterprise sales leadership who understood how to navigate complex deals. “Hire experienced enterprise AEs, build out sales engineering, create proper deal review processes,” Umaimah says. These leaders brought playbooks, coaching, and credibility that helped the broader team develop enterprise selling capabilities.

Measuring Success Beyond Revenue

The compensation restructuring’s success couldn’t be measured purely in closed revenue. Opal needed to track leading indicators: enterprise pipeline growth, average deal size, sales cycle length, executive engagement, multi-year commitment rates, and expansion potential.

These metrics revealed whether sales team behavior was actually changing. Were reps investing time in strategic accounts? Were they building relationships with economic buyers? Were they pursuing contracts with stronger expansion potential? Revenue metrics lag—behavior metrics lead.

The data validated the approach. Average deal size increased. Enterprise pipeline grew. Sales cycles lengthened initially but stabilized as the team developed enterprise selling skills. Most importantly, the quality of closed deals improved—higher retention, better expansion rates, stronger executive relationships.

What This Means for Compensation Design

Opal’s compensation restructuring demonstrates a broader principle: incentive alignment isn’t about paying people more—it’s about changing relative economics to make desired behaviors personally profitable. Sales teams will always optimize for their economic interests. The question is whether company interests and individual interests align.

For technical founders scaling into enterprise, this means auditing compensation structures as strategy evolves. The comp plan that worked for product-led growth might actively undermine enterprise strategy. Small deals with fast cycles are economically attractive to sales reps when commission structures are neutral to deal size.

“We structured our sales comp to reward larger deals with better margins,” Umaimah notes. The specifics matter—commission rates, accelerators, bonus structures, strategic metrics. But the principle is universal: your sales team will optimize for whatever you pay them to do. If you want enterprise focus, make enterprise deals significantly more profitable for individual reps than volume-based mid-market sales.

The companies that successfully transition from mid-market to enterprise don’t just change messaging and hire new reps. They restructure the economic incentives that drive daily sales behavior—making strategic account focus the rational, profitable choice for every member of the sales organization.