What are the Key Issues resolved through Head of Sales/CRO assist?

  1. Quota attainment
  2. Forecast accuracy
  3. Win-rate improvement
  4. Team-building & development
  5. Operational executive communication

Booking/Sales quota attainment Highest ranked issue


Working back from right-to-left, we inspect the performance of the sales team in all areas of the buyer's journey from initial interest, mutual discovery, confirmation of value alignment, comparison to alternatives, negotiation of terms & conditions, pricing and packaging, and contracting with expectations of on-boarding to first impact of value.

Measure & test

In each of the sales stages, we are measuring performance with best-practices of peer performance and implementing changes through small, incremental sprints designed to empower change and gain visible results correlated with actions.


These internal actions are documented in the operating playbook for consistent, predictable performance from the sales team and serve as a unification element across customer engagements in the sales cycle. This is ideal for on-boarding new sales team members for faster ramp-to-productivity and cross-training with other functions for a consistent brand experience.

Typical challenges in quota attainment for Sales leaders and their teams
Only a few sellers are at plan Great month/qtr followed by miss Too many slips
Not enough leads Getting ghosted Poor quality leads
Stalled decisions Not enough meetings Loss to competitors
Not enough pipeline coverage Accountability for results is absent Missing attainment action-plan
Inadequate training to perform as expected No common deal language Win/Loss ratio is less than 20%
Aggressive discounting and panic closing actions Meeting agenda management Ineffective negotiating outcomes

Forecast accuracy

Typical challenges in forecast accuracy for Sales leaders and their teams
Missed bookings call for period Unable to forecast for current period Rapid loss of forecast revenue at end of period
Struggle in bridging gap to plan Inability to forecast following future quarter Inconsistent alignment of sales cycle and forecasted booking
Behind in year-to-date bookings Insufficient pipeline quality & quantity Unable to evidence quota alignment with actual production capability
Reliance on key opportunities each period to make plan Managing too many low-quality opportunities Use of subjective terms in forecasting booking attainment


What are the attributes of previously won opportunities? What were the discrete stages throughout the sales process? Mapping these actions and steps set the foundation of common language when discussing opportunities and related revenue forecasting as not all opportunities are equal; some are statiscally higher candidates for closing within the sales cycle at known contract values.


Building on the attributes of successfully closed-won opportunities, a common language is developed when describing individual opportunities for risk-profiling and related prioritization of efforts & resources. Pipeline reviews provide clear insight to opportunity health and forecast status based on known criteria of what is required (or must-happen) for this opportunity to close and book as contract at the deployment date.

Use in all conversations

Using a common opportunity language across the organziational functions allows marketing, product, customer-success, finance, and executive teams to understand and communicate expectations in booking and revenue values relative to time periods, increasing stakeholder confidence in the value-creation production and delivery.

Get started quickly



  • 5-pack of 60-minute 1:1 sessions
  • Scheduled as needed
  • Covers scope of responsibility
  • Strategic and Tactical

Monthly Retainer


  • Coaching contract for specific OKR(s)
  • 15 to 60-min sessions
  • Schedule as needed, or recurring weekly
  • Billed monthly until cancelled
  • 15-day cancellation notice
Let's discuss