Onboarding Your First Sales Hire: A 30-60-90 Day Blueprint for Accountability

Bringing on a salesperson is one of the riskiest—and most rewarding—moves a consulting founder can make. Get it right and you’ll unlock new revenue; get it wrong and you’ll hemorrhage time, money, and morale. A structured 30-60-90-day plan not only fast-tracks ramp-up but also embeds accountability so you can decide early if your new hire is a keeper.

Why a 30-60-90 Plan Matters

• Clarity & Confidence: New hires know exactly what to learn, practice, and deliver in each phase.

• Measurable Progress: Clear milestones and metrics let both manager and rep track success (or red flags) from day one.

• Early “Keeper” Decision: With defined checkpoints, you’ll quickly see if a rep is hitting stride or if you need to pivot—before six figures in salary has been spent Zendesk.

Phase 1: Days 1–30 “Learn & Observe”

Objective: Build foundational knowledge & begin simple, low-stakes activities.

1. Sales Process Deep-Dive

   • Map your firm’s end-to-end sales process: prospect → discovery → proposal → close → post-sale delivery.

   • Shadow calls and ride-along on demos with veteran sellers.

2. Market, Buyer & Offering Familiarity

   • Study ideal customer profiles: industries, company sizes, personas, common pain points.

   • Review core service offerings, case studies, ROI examples, and pricing structures.

3. Tools, Collateral & Admin

   • Get comfortable with the CRM, sales playbooks, proposal templates, and expense policies.

   • Complete all administrative onboarding (systems access, travel policy, company handbook).

4. Accountability Checkpoint (Day 30):

   • Quiz on process steps, value proposition, and CRM hygiene standards.

   • Manager “go/no-go” call: Is knowledge solid enough to pick up the phone?

Phase 2: Days 31–60 “Practice & Engage”

Objective: Move from observation to execution under close coaching.

1. Territory & Pipeline Building

   • Finalize a target account list (ICP filtering, existing budgets vs. white-space opportunities).

   • Begin outbound prospecting: cold emails, LinkedIn outreach, initial discovery calls.

2. Discovery & Solution Crafting

   • Lead at least 3 mock discovery calls with a peer or manager, using real case scenarios.

   • Draft proposals for two hypothetical opportunities, focusing on ROI messaging.

3. Presentation & Negotiation

   • Deliver one live demo or pitch with manager feedback.

   • Role-play negotiation scenarios: discount requests, scope creep, contract terms.

4. Manager “Ride-Along”

   • Co-sell on at least two live opportunities, then debrief: what worked, where to improve.

5. Accountability Checkpoint (Day 60):

   • Review activity metrics: calls made, meetings set, proposals sent.

   • Qualitative evaluation: quality of discovery questions, solution fit, objection handling.

   • Decision: Is performance trending toward target? If not, plan a corrective “Performance Improvement Plan” or consider parting ways.

     
     

Phase 3: Days 61–90 “Independence & Growth”

Objective: Own the full sales cycle and begin closing real business.

1. End-to-End Deal Ownership

   • Manage 2–3 live opportunities from first call through contract.

   • Track progress in CRM with accurate sales stages, next-steps, and close dates.

2. Account Development

   • Identify upsell or cross-sell potential in existing accounts.

   • Draft a mini-account plan for one current client: objectives, stakeholders, timetable.

3. Advanced Selling Skills

   • Facilitate a negotiation with a real prospect under light manager support.

   • Conduct a business-review presentation for an existing customer to demonstrate value delivered.

4. Self-Directed Learning & Coaching

   • Attend one external sales webinar or workshop and share key takeaways.

   • Pair with a mentor for fortnightly best-practice sharebacks.

5. Keeper Evaluation (Day 90):

   • Quantitative: Has the rep hit ≥75% of their 90-day activity and pipeline targets?

   • Qualitative: Does the rep demonstrate consistent professionalism, coachability, and cultural fit?

   • Outcome: Confirm as long-term team member, extend probation with clear goals, or part ways.

Embedding Accountability Throughout

• Weekly 1:1s with a clear agenda: activity review, pipeline health, skill gaps.

• Scorecard Metrics: Track calls, meetings, proposals, win rate, average deal size.

• Transparent Feedback: Real-time coaching on calls and emails via screen-share or call-recording reviews.

• “Red Flag” Triggers: Missed activity targets for two consecutive weeks should prompt an immediate performance discussion.

Beyond Day 90: Continuous Improvement

• Transition into regular sales rhythm: monthly forecasting, territory planning, and ongoing professional development.

• Encourage peer-to-peer best practice sessions and periodic ride-alongs to reinforce process.

Remember: Effective onboarding is not a “nice to have”—it’s the critical first step in ensuring your new sales hire turns into a revenue-generating machine rather than a costly experiment.

Implement this 30-60-90-day playbook with rigor and you’ll know within three months whether you’ve landed a top performer—or if you need to reboot.