Sales teams live and die by the numbers, but quota attainment alone doesn’t tell the full story. A strong revenue engine isn’t just about closing deals — it’s about building a predictable, scalable system that balances pipeline generation, sales execution, and cross-functional accountability. Without a structured approach, companies risk last-minute scrambles, inefficient forecasting, and a sales culture that leans too heavily on heroics instead of process.
In our February 13 AMA with Madrona portfolio company CEOs, we dug into the mechanics of running a disciplined GTM motion beyond just hitting quota. From pipeline management and sales leadership to compensation structures and forecasting strategies, this discussion highlighted the key levers every founder and GTM leader should pull to build a high-performing revenue organization. This post breaks down the biggest takeaways, offering a blueprint for driving scalable and predictable growth.
Why Pipeline is More Than a Sales Metric
In a fast-scaling business, pipeline isn’t just a number for sales to track — it’s the company’s lifeline. A healthy pipeline reflects the efforts of sales, marketing, product, and finance working in sync. One of the most frustrating inefficiencies in GTM organizations is wasted time debating pipeline numbers rather than taking action. Without a single source of truth, teams spin cycles reconciling conflicting data instead of making real decisions.
This is why pipeline should be owned by sales ops, validated by finance, and treated as a shared company-wide asset. It ensures that when teams come together, the conversation is about insights and action — not discrepancies in the data.
To assess pipeline health, track:
- Total pipeline and weighted pipeline – A leading indicator of revenue trends.
- Change in pipeline over time – Is it growing, too many deals lost day 1 of new quarter?
- Touch frequency – Deals need movement; if they’re sitting untouched, they’re at risk.
- Next steps scheduled – Active deals should always have a next engagement planned.
Implement a Pipeline Council for Cross-Functional Accountability
Pipeline isn’t just a sales responsibility. It’s a company-wide asset. Establishing a weekly pipeline council aligns sales, marketing, finance, and product on how to fill, manage, and convert pipeline effectively.
Rather than each function presenting its own version of the numbers, ops should provide a single, unified pipeline report that highlights trends, gaps, and forecasts. The focus should be on leading indicators (MQL-to-SQL conversion, deal velocity, ACV trends) to drive proactive actions. This ensures alignment across GTM teams and drives accountability.
In these meetings, leaders should discuss their contributions and commit to concrete actions that improve pipeline health and deal velocity. Sales, marketing, finance, and product should all understand how their efforts impact pipeline generation. And every leader should leave with 2-3 measurable steps to improve pipeline health.
Clean and Structured Pipeline Management is Non-Negotiable
Pipeline hygiene is critical to forecast accuracy and revenue predictability. By the fifth business day of every new quarter, all pipeline data should be clean: accurate values, stages, and close dates. Watch for red flags like:
- A high number of deals clustering at the last day of the quarter.
- Deals consistently rolling over quarter to quarter without closing.
- A gap between closed-lost reasons and actual pipeline movement — are reps over-qualifying bad deals?
By monitoring these factors, leaders can identify whether deals are slipping due to poor qualification, weak sales execution, or misalignment in marketing, product, or pricing.
Activity Drives Pipeline — Measure It
Pipeline doesn’t generate itself. Teams should use sales engagement tools and CRM analytics to track rep activity:
- Meetings booked per week – A leading indicator of future pipeline.
- Follow-up rates – Are deals progressing or stalling?
- Prospecting cadence adherence – Ensure teams aren’t just working inbound leads.
Reps should be accountable not only for closing current-quarter deals but also for consistently booking pipeline for future quarters. Companies that consistently track and enforce these behaviors ensure stronger pipeline coverage and long-term revenue stability.
Seasonality and Variability
Accurate forecasting requires more than just looking at pipeline coverage ratios. Establishing historical pipeline benchmarks helps determine the appropriate coverage needed at the start of a quarter. Enterprise deals, in particular, require early contract negotiations — 60-90 days before the quarter ends — to avoid last-minute legal and IT bottlenecks. Additionally, leaders should analyze past trends to account for seasonality and ensure consistent pipeline generation throughout the year.
Front-Load Sales Execution to Reduce Quarter-End Risk
Instead of relying on last-minute end-of-quarter deal pushes, high-performing teams front-load execution. Leaders should analyze historical close rates by month to set realistic pacing expectations and, if necessary, introduce spiffs to encourage early-quarter deal closures. By improving pipeline pacing and ensuring early legal approvals on enterprise deals, companies can increase revenue predictability and reduce quarter-end risk.
Focus on Rep Attainment vs. Quota Achievement
A team hitting quota means nothing if only a handful of reps are carrying the load. Strong sales orgs ensure 70-80% of reps are hitting 70-80% of their number. If rep attainment is low, assess:
- Onboarding effectiveness – Are new reps ramping efficiently?
- Territory balance – Are some reps over-assigned while others struggle with whitespace?
- Enablement programs – Track leading indicators like time to first meeting and time to first deal.
If 70% of your revenue is coming from only 20% of your reps, you don’t have a scalable sales engine — you have a hero-driven model that’s bound to break.
Align Compensation Plans with Business Objectives
Sales comp plans should be simple and aligned with strategic goals. Best practices include:
- No more than three components – Too many variables dilute focus.
- Using kickers and gates – Reps must hit a minimum net new logo count to qualify for accelerators.
- Avoid backloaded comp plans – Ensure even weighting across quarters to prevent last-minute revenue scrambles.
Define the CRO’s Compensation with Both Growth and Efficiency Metrics
A well-structured CRO compensation plan balances new logo acquisition, retention, and expansion. Compensation should be structured with thresholds to ensure leaders don’t qualify for full earnings unless they meet both new revenue and retention goals. As business priorities evolve, CRO compensation should be adjusted accordingly, especially when expanding into new products or regions.
Build a Culture of Action-Oriented Sales Leadership
Strong CROs aren’t just pipeline managers tracking numbers — they drive accountability across the entire GTM organization. Effective leaders proactively solve problems, partner with marketing to refine demand generation strategies, and work with product to ensure roadmap priorities align with sales success. Companies should prioritize sales leaders who not only manage existing processes but also improve efficiency, drive change, and ensure long-term scalability.
Looking Forward
Scaling revenue isn’t just about meeting quarterly targets—it’s about building a machine that sustains growth year after year. By refining how pipeline is managed, ensuring comp structures drive the right behaviors, and holding leaders accountable for efficiency and execution, founders can set their teams up for long-term success.
This guide came from our February portfolio company GTM sessions. Keep an eye out for takeaways from April’s session, where we’ll dive deeper into what leaders should know about fundraising in 2025.