Short Answer
During the first 90 days with a fractional sales leader, they run a gap assessment to find out where your biggest gaps actually are. From there, the 90 days break down by month. Month one puts the assessment’s plan into motion, month two tightens it with targeted coaching and accountability, and by month three, the new system is running on its own. What that looks like depends on whether you bring on a fractional sales manager or an executive-level FSL, a CRO, or a VP of Sales.
Key Takeaways
- Your fractional sales leader builds their own gap assessment, and you should get it in writing.
- The first 30 days put that assessment into action: a fractional sales manager starts pipeline reviews and coaching immediately, a fractional CRO builds out the strategy the assessment found, and a fractional VP of Sales turns their pipeline and forecasting audit into an improvement plan.
- Days 31 to 60 tighten what’s already in motion: coaching gets specific, and targets tighten for a Manager, the comp plan and go-to-market approach roll out for a CRO, process changes get implemented for a VP.
- By day 90, the team is stable and running on a real process without you having to force it.
- Your fractional sales leader doesn’t disappear at day 90. Coaching, pipeline reviews, and refinement continue until your team either grows into a full-time hire or the processes run entirely on their own.
The Gap Assessment
The first 90 days with a fractional sales leader begin with a gap assessment.
Fractional sales leaders use the gap assessment to tell if the biggest gaps are in performance, like your reps not hitting numbers. Or possibly the gap hurting your company the most is a gap in resources because your reps and managers don’t have the right tools and coaching to do their jobs and meet their goals. The gap could be in the process itself, which lacks a repeatable system for reps to use.
Many sales teams have gaps in all three, but it takes the assessment from an FSL to truly determine what needs the first, most immediate work.
Your FSL takes the time to hear from you and your reps to see the problems for themselves. They build the assessment and review it with you. What that assessment looks like largely depends on which type of FSL you work with.
A fractional sales manager’s assessment takes a close look at your sales team and reps. They look at day-to-day processes and weak spots that need improvement.
An executive-level FSL, whether that’s a fractional CRO or a fractional VP of Sales, comes in to focus on your revenue engine at a higher level.
A CRO takes the widest view, assessing everything from management to strategy.
A VP of Sales stays more focused on the sales process itself, auditing your team’s daily processes and determining if they’re the best fit or need restructuring.
Once the assessment is complete, ask to see it in writing. That document becomes your roadmap. It tells you exactly what the next 90 days will fix, in what order, and how you’ll know it’s working.
When you’re satisfied that the assessment is actionable, the 90 days begin.
The First 30 Days: Plans in Motion
The gaps in your sales processes didn’t open overnight, and the first 90 days with a fractional sales leader don’t close them overnight either.
Now that your FSL has completed their initial assessment and built action plans, the first 30 days are about putting those plans in motion.
If you brought on a fractional sales manager, your sales team gets the focus. They will immediately conduct regular pipeline reviews with you and your reps. They may even shrink your pipeline, especially if it’s stuffed with unrealistic prospects that serve as filler. They’ll separate the viable prospects from the funnel fantasies.
Coaching begins right away. Your FSM starts immediate one-on-ones with your reps. They listen to calls and review deals that closed and deals that didn’t. Reps get coached on the successes and failures to build stronger tactics.
If you brought on an executive-level FSL, your CRO takes everything the assessment found and builds you a strategy that identifies who to sell to, a repeatable process for your team, accurate forecasting, a pay structure that drives the right behavior, alignment between sales and marketing, and reporting that holds up for your board and investors.
A VP of Sales works at a similar level but stays focused specifically on your sales function. In their assessment, they have audited how deals move through your pipeline, your forecasting methods, and your frontline managers, and in month one, the improvement plan for each begins.
By the end of month one, you have a specific roadmap for your sales process, your forecasting, and your management team.
The first month with a fractional sales leader is a crucial action period. You’ll end it running the exact plans, playbooks, pipeline updates, and forecasts to get revenue moving again.
Days 31 to 60: Tracking Accountability
Your team has entered month two with your FSL on board.
This is also when accountability starts getting tracked much more closely. It’s an adjustment period for you and the team, because your FSL is changing your processes and standards. Some of your team might push back, but that just means the accountability is working.
A fractional sales manager spends month two tightening your team’s targets, built on the findings from your gap assessment and where you want your company to go.
This is where coaching gets specific.
Your FSM has listened to enough calls to know where each rep struggles.
Whether your sellers are battling anxiety around cold calling, facing price objections from prospects, losing the call somewhere in the conversation, or doing more talking than listening, they get coached on the area of their prospecting that needs the most work. Month two also ends with consistent, reliable pipeline reviews.
An executive-level FSL spends month two putting the month-one strategy to work.
A fractional CRO starts rolling out the comp plan and go-to-market approach they built, with cross-departmental alignment on pay structure, who to sell to, board reporting, and overall direction.
A fractional VP of Sales spends month two implementing the process changes from their audit. Your fractional VP tightens forecasts, puts the new playbook to work, and starts developing your managers hands-on.
Days 61 to 90: It All Starts Working
By the third month, your fractional sales leader has your team running processes that work, and you have a clear picture of how to continue leading your team and your company forward.
A fractional sales manager now has your sales team running on the processes and training they’ve received in the first two months. Your FSM holds your reps accountable to their activity numbers every week.
Your FSM has listened in on your reps’ calls and coached them through what was working and what needed work. Your sales team improved their work with coaching catered to their specific growth areas.
Now they are confident in making cold calls because their one-on-ones with your FSM gave them skill-building techniques to overcome buyer resistance and close more deals. By the end of this month, your forecast reflects the reality of what your team is working toward.
An executive-level FSL has your company running on the strategy or process they built. A fractional CRO’s work is often still in progress at this point, since rebuilding revenue strategy at the company level takes longer than a few months.
A fractional VP of Sales, by contrast, usually has your team running the new process without their direct enforcement by this point. Forecasting is strong and accurate, frontline managers are running things confidently, and the playbook is a staple your managers use without a VP standing over them.
From 90 Days to Now What?
Any of these engagements can run longer than 90 days depending on the size of the change involved. But in three months, your company and team have made real progress with your FSL.
You’ve had the first 90 days with a fractional sales leader to see growth and progress, but better doesn’t mean best. It means that, for now, things are running smoothly and steadily.
But the truth is, your fractional sales leader doesn’t disappear at day 90.
Coaching continues, pipeline reviews keep running, and your FSL continuously refines the processes they just built as the team adapts and your company’s needs evolve. Your team made strides to improve, and that improvement keeps compounding as long as your FSL is still on assignment with you.
That day you no longer need an FSL usually comes when your team has grown enough to justify a full-time hire. Your FSL remains on site to help you recruit and eventually hand off the playbook.
Once your processes have become second nature to your team and run without anyone enforcing them, or your business has changed shape enough that what you need next looks different than what got you here, your FSL’s assignment will come to a close.
Until then, you and your FSL continue to enforce the high standards you’ve built. Your team respects the consistency, and they’re better at their jobs because of it.
You can continue to patch the problems yourself without addressing the real needs, but doing so puts your company at greater risk. Minimize that risk and bring in a proven leader who has already built what you’re trying to build. Talk to a Sales Gravy fractional sales leader and find out where the gaps are and how to fix them.
Frequently Asked Questions About The 90 Days with a Fractional Sales Leader
They build a gap assessment by reviewing your pipeline, your playbook, your processes, and your reps, and talking directly to your team. Ask for that assessment in writing before they start, so you know exactly what the next 90 days will fix and on what timeline.
No. A fractional sales manager works directly with your team on pipeline and coaching. A fractional CRO looks at your entire revenue engine, strategy, comp plan, and go-to-market approach. A fractional VP of Sales sits between the two, focused specifically on your sales process and forecasting. The 90-day arc is the same shape for all three, but the work inside it is different.
Often, yes, and that’s a good sign, not a bad one. A fractional sales manager typically finds prospects that were never real, and removing them gives you a pipeline number you can actually trust instead of one that was inflated by filler.
Not a transformed sales team. A stable one. Pipeline reviews happening on schedule, coaching that’s targeted instead of generic, accurate forecasting, and a team running the process without you or your fractional leader forcing it every week.
Not always. A fractional CRO engagement, in particular, often runs longer than 90 days since strategic change takes more time to fully implement. A fractional sales manager or VP engagement may wrap closer to the 90-day mark, depending on what your team needs.
Staying engaged, not going it alone. Your fractional sales leader typically doesn’t wrap up at exactly day 90. Coaching, pipeline reviews, and process refinement keep running until your team either grows enough to justify a full-time hire or the standards become second nature and run without anyone enforcing them.
