1-on-1 B2B Sales Rep Coaching with AI Supported Deal Prep
Sales reps spend 60% of their time on non-selling tasks. We install AI-supported prep and follow-through workflows, then coach your reps 1-on-1 to turn that reclaimed time into higher-trust conversations and cleaner next steps.
from Non-Selling Tasks
New Habits
Irrelevant Outreach
Accountability
Higher revenue per rep through better preparation
We don't sell "coaching." We sell measurable improvements in performance and time-to-productivity. Three shifts happen in every seat:
Admin to selling time reclaimed
Reduce non-selling load by installing AI-assisted workflows for research, prep, follow-up, and CRM updates—while maintaining human verification. Target the "60% non-selling tasks" reality directly.
Conversation quality and trust
Improve relevance, problem framing, and next-steps discipline so outreach and discovery create buyer confidence. Counter the "73% avoid irrelevant outreach" pressure with preparation that proves you did the work.
Deal execution discipline
Increase win rate and quota attainment by moving from ad-hoc feedback to structured, dynamic coaching systems. CSO Insights reports this approach materially outperforms random coaching.
B2B teams selling complex solutions
5 to 50 Sales Reps
Large enough that operating rhythm matters, small enough that CEO or founder can approve quickly. You've outgrown founder-led sales but aren't ready for a full-time VP of Sales.
Complex, Relationship-Driven
Multi-month sales cycles. Multi-stakeholder deals. Solutions that require discovery and trust, not transactional volume. Your buyers can tell when you didn't do the homework.
Ready for Discipline
Founder carrying sales and needing to hand it off. Inherited sales team without clear process. Preparing for funding round and needing "revenue discipline." Flatlined revenue after AI tool adoption.
What each coaching seat includes
Weekly 1:1 Coaching Session (60 min)
Focus rotates across deal strategy, skill building, messaging, and operating discipline—grounded in the rep's live pipeline, not generic scenarios.
Async Call & Message Review
One call (or transcript) and one outbound/follow-up message reviewed weekly with structured feedback. Modern coaching through conversation intelligence.
AI Workflow Installation
Weekly "workflow build" where coach and rep implement one AI-assisted method: research briefs, discovery prep, post-call summaries, or CRM updates—done with the rep, not handed to them.
Human Verification Checklist
One-page checklist the rep uses before any AI-supported output reaches a buyer. Protecting credibility at the point of execution.
Manager Visibility
Biweekly manager note (5-7 bullets): what changed, what is blocked, which workflow was installed, which deal risks are real. No "tattleware," just operational clarity.
Rep Operating System
Graduation deliverable: weekly cadence, prep-to-follow-up workflow, verification checklist, messaging architecture, and deal brief template.
Week-by-week implementation
8 weeks to install habits. Long enough to build muscle memory, short enough to prove value fast.
- Collect 2 recent call recordings or transcripts (or live observation)
- Collect 3 outbound examples and 2 follow-ups
- Export current pipeline view (stages, next steps, close dates)
- Identify 2 metrics to move in 8 weeks (meetings set, discovery-to-next-step rate, follow-up cycle time, win rate)
Critical foundation: Coaching is most valuable when consistent and measurable, not random.
Install "prep to follow-up" workflow:
- Pre-call brief (account facts, hypotheses)
- Discovery question set tied to hypotheses
- Post-call summary and follow-up draft with clear next step proposal
- Add verification points so rep checks facts and tone before sending
- Rewrite rep's discovery opener and problem framing pattern
- Build qualification decision tree tied to complex solution context (multi-month cycle, relationship-driven)
- Use AI to generate hypothesis paths and counter-hypotheses, then choose human judgment path
Create reusable message architecture:
- The "why you, why now" relevance hook
- Proof of preparation (one specific insight, not trivia)
- The question that earns a reply
- Edit AI drafts for emotional correctness and context
- Implement "clean next step" routine: decision, owner, date, mutual value
- AI-supported "deal brief" format (one page) for internal deal reviews
- Tighten decision context and operating rhythm
- Map the buying group and build credible path to internal consensus
- AI-drafted persona-specific "what they care about" bullets, validated with actual call content
- Coach on building coalition and managing detractors
- Install mutual action plan template (without sounding scripted)
- Negotiation posture and procurement readiness
- "No surprise close" discipline
- Complex deal navigation for multi-month cycles
- Review which workflow saved the most time and improved conversion
- Remove tools, templates, or behaviors that create noise
- Consistent with "not more tooling" stance
- Optimize the tech stack for readiness, not capability
Produce the Rep Operating System:
- Weekly cadence and prep-to-follow-up workflow
- Human verification checklist
- Messaging architecture
- Deal brief template
Next step recommendations: Continue 1:1 monthly for deal strategy, expand to more seats, or upgrade to Fractional Revenue Leadership for org-wide installation.
Choose the accountability level
Three tiers, each one-to-one, with different levels of review depth. All seats are 8 weeks with option to continue month-to-month.
- 1 x 60-minute session weekly
- Async call/message review biweekly
- AI workflow installation (one per week)
- Human verification checklist
- Biweekly manager updates
- Rep Operating System at graduation
- 1 x 60-minute session weekly
- Async call/message review weekly
- Priority AI workflow installation
- Human verification checklist + refinement
- Biweekly manager updates with deal risk flags
- Rep Operating System at graduation
- LinkedIn/messaging optimization
- 1 x 60-minute session weekly
- Async call/message review weekly
- 1 x Live deal support slot per month (call joining/prep)
- Advanced workflow automation
- Multi-stakeholder strategy sessions
- Weekly manager updates
- Rep Operating System + advanced templates
Why this isn't "sales training"
Dynamic vs. Random Coaching
CSO Insights reports that structured, dynamic coaching approaches outperform random or informal coaching. We operate on a fixed cadence with specific workflow installation, not "call me when you have a problem."
Human Verification Points
AI supports research and preparation; judgment stays accountable to the rep. Every workflow includes verification checkpoints so your team doesn't trade speed for credibility.
Tool-Agnostic Workflow Design
We don't sell software. We install workflows that work with your existing stack. If you have CRM and email, we can operate. Forrester warns that tools outpace readiness—we fix the readiness.
Delivered by the Founder
When you engage Get 'er Done, you get Timothy Doelger—not a rotating bench of junior coaches. Nuclear submarine veteran. 30 years B2B sales. Direct accountability.
Questions about the coaching program
Ready to reclaim selling time?
Start with one seat. Prove the model. Scale what works. Nothing happens until the check clears.