The Hard Truth About Scaling Sales According to a CRO: What Actually Works (And What Doesn't)

Most sales organizations don’t struggle because of bad reps. They struggle because of bad systems, unclear processes, unreliable data, and ineffective pipeline reviews.

In a recent conversation with Chief Revenue Officer at Fospha, Tom Sheepshanks, who leads a high-growth sales team, key insights emerged about what actually drives performance and what holds teams back. These are the takeaways.

 

 

2. Sales teams can't adopt messaging they can't remember

Product marketing teams invest significant effort into refining messaging. But that messaging often doesn’t make it into real sales conversations.

The issue isn’t intent, it’s tracking. Without a clear way to measure adoption, it’s impossible to know if messaging is truly being used.

To bridge the gap:

• AI can analyze sales conversations to verify if new messaging is being used
• Marketing can adjust messaging based on real adoption rates
• Sales leaders can track messaging effectiveness over time

If close rates aren’t improving, is the messaging ineffective, or is it simply not being used? Without measurement, there’s no way to tell.

3. AI shouldn't make sales decisions but it should confirm actions

AI is often positioned as a tool for decision-making, but its real value is in decision-confirming.

A poor AI system tells the team: “The customer has no budget.”

A useful AI system provides clarity: “The rep has had a budget conversation.”

There is a fundamental difference between an AI tool that dictates actions and one that verifies what has already happened.

Trust in AI grows when it is used to confirm key deal details, rather than attempting to replace sales judgment.

4. Tactical problem-solving beats gamification every time

Leaderboards and competition-based motivation structures are often seen as key drivers of performance. Yet many sales leaders are moving away from traditional gamification models.

Instead of ranking top closers, more effective incentives include:

• Recognition for the best new objection-handling tactic
• Rewarding the most creative deal rescue
• Highlighting improvements in qualification consistency

The best salespeople are motivated by progress, not points. Structuring incentives around execution and skill development has a greater long-term impact than simple ranking systems.

5. Sales performance shouldn't be a private conversation 

Coaching and performance reviews are often treated as individual conversations, but the most effective teams take a public coaching approach.

• Calls are reviewed as a team
• Challenges are surfaced in pipeline reviews
• Reps coach each other

When coaching is shared, the entire team benefits from collective learning. If one rep struggles with an objection, others should learn how to handle it. Growth happens faster when teams learn together rather than in isolation.

6. Strategic decisions should be based on data, not gut feel

A recent shift in sales strategy for Tom involved moving technical conversations pre-signature to prevent post-signature roadblocks.

This change was made after analyzing deal progression patterns and identifying that implementation teams were not engaged early enough.

Key benefits of this approach:

• Technical buy-in before contract signing
• Reduced delays in implementation
• More predictable deal velocity

When strategy is informed by real deal data, rather than assumptions, improvements happen faster.

7. Sales leaders need to stop chasing the wrong metrics

Sales teams often default to tracking deal value as the primary indicator of success. However, focusing solely on revenue overlooks critical performance drivers.

The three most valuable sales metrics:

• Close rate – How many deals are actually converting?
• Deal velocity – How quickly are deals progressing?
• Execution consistency – Is the team following a repeatable process?

Revenue is an outcome, but process drives results. By shifting focus to execution, teams build sustainable growth.

8. Your sales team doesn't need a boss. They need a system.

Sales teams perform best when they have clarity, structure, and autonomy, not when they are micromanaged.

A strong system includes:

• Psychological safety—so reps are comfortable addressing challenges openly
• Structured daily reviews—so teams know what’s working
• Clear accountability—so every rep takes ownership of execution

Micromanagement doesn’t scale. A system that enables clear, repeatable success does.

9. Reflection separates good sales teams from great ones

Most sales teams focus on future deals but spend little time analyzing past performance.

Regular reflection should be a core part of sales strategy:

• Monthly reviews track mid-level trends in deal progression
• Quarterly deep dives identify patterns in lost deals
• Comparison across past quarters helps refine future strategies

Improvement happens when teams learn from what hasn’t worked, not just from what has.

Final thought: Sales success comes from consistency, not individual genius

The highest-performing sales teams aren’t built on a few superstar closers. They succeed because they have:

• A clear, repeatable process
• A data-driven feedback loop
• A team-wide approach to learning and coaching

Scaling sales isn’t about finding the most talented individual contributors. It’s about creating a system where every rep can consistently perform at their best.