You just hired a great salesperson. They have a solid track record, they’re excited, and the whole team loved them during the interview.

But two weeks in, they’re sitting at their desk looking lost. They aren’t sure if what they’ve read so far is enough to get it right in front of customers, and their calendar is still empty.

On Day 1, they met their manager and received a spreadsheet full of “useful” links: Confluence pages, recorded webinars, product courses, and a list of people to meet. A buddy was assigned, but they’ve only met once. Colleagues said, “I’m here if you have questions—just Slack me!”

Is this enough? No.

In most cases, a new hire “doesn’t know what they don’t know.” It is often pointless for a manager to simply say: “Ask me when you need something.”

Your job is to set them up for success from Day 1. A manager must leverage internal help—People Team, RevOps, Enablement, Marketing, CSMs—and engage the “whole village” to walk the newbie by the hand for at least the first month.

Build relations by collaborating cross-functionally to develop an onboarding plan. Build the experience you wish you had when you first started your career.

You might say: “But we hire seniors, not just juniors. You can’t spoon-feed them.”

Well, it is better to have a system and fast-track a senior through it in a week than to let them flounder based on assumptions. Assumptions are expensive.

In Series B or C SaaS companies, senior leadership rarely sees a sales onboarding plan as a top priority. Enablement is often spread thin.

Because the Front Line Manager is ultimately responsible for adoption, ramp time, and quota, you must be a proactive leader. Build a business case to allocate resources before the massive hiring phase.

The spreadsheet approach is a silent killer :

1️⃣ Burn Cash

You are paying a high salary for someone to sit in a room and watch old videos. That’s a $15k-per-month mistake.

2️⃣ Lose Trust

When a new rep realizes the onboarding is a mess, they lose faith in the company. They think, If they can’t even spend time and effort in setting me up for success, how are they going to support my customers?

3️⃣Revenue Lag

If it takes 6 months to ramp a rep because they are left to figure it out on their own, you’ve lost half a year of quota. For a team of 5, that’s millions of dollars in missed revenue.

Confusion doesn’t just slow people down; it kills the culture you’re trying to build.

Look at your current onboarding. Be honest:

Level 0 (The Dump): You send links and recordings and expect them to figure it out. You think a top rep’s time is “too expensive” to use for buddying.

Level 1 (The Checklist): You have a list of tasks. You check if they are done, but you don’t check if the rep can actually do the work.

Level 2 (The Architect): You have a sequential plan. You use role-plays and certifications. Nobody talks to a customer until they’ve proven they can handle the heat.

To get your hire hitting quota fast, stop the endless video loops. If you have resources, turn them into a searchable page—or better yet, plug them into an internal AI so reps can ask questions in a controlled space before coming to you.

Integrate these into their onboarding plan:

1️⃣ The Sequential Pitch

Shadowing is often passive and boring. Instead, give them the Pitch Deck, the Scorecard, a “what good looks like” recording, and a 1-pager on the why behind the structure.

• Week 1: They learn the “Elevator Pitch” and record a version (no scripting!) by Friday.
• Week 2: You provide feedback in your 1:1.

2️⃣ The Role-Play Simulator

Before they touch a real lead, they role play with AI, with a peer, with the Manager. Based on role SDR, AE these role plays are tailored to their day-to-day job across the sales process, sales methodology, buyer’s journey…

• The Mock Call: You (the manager) act as the customer. Don’t make it easy.
• The Feedback Loop: After the call, don’t tell them what they did wrong. Ask them: “How do you think that went? What would you change?”
• The Validation: They repeat this until they hit a “Pass” score. This is where the real learning happens—not in a Confluence doc.

3️⃣ The Buddy Boundary

A buddy program shouldn’t be a 24/7 help desk; that burns out your top performers.

• The Schedule: Meet twice in Week 1, then once weekly in Weeks 2 and 3.
• The Goal: The Buddy is there to show them what good looks like, what to avoid, what works and why.

The Responsibility: If the new hire has a question, they should check the docs first, then ask the Buddy, then come to you. This teaches them to be resourceful from day one.

If you are looking to grow your team, now is the time to recreate your onboarding plan. If you don’t have an Enablement team yet, brainstorm with your latest hire. Ask what they wish they’d had, and delegate them to help draft the activities.

Giving someone information is not the same as teaching them a skill.

Teaching is about removing the training wheels one inch at a time. Let them wobble so they learn to balance. If you just provide a manual on “how to ride a bike,” they’ll never leave the driveway.

Give them the space to fail. Then, be there to pick them up and help them win.

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See you in the Next Success Sprint,

​Sonia Pupaza | Founder, Empower Value | Sales Leadership Expert

I help high-performing ICs and new managers become successful leaders. If you are looking to invest in your future leaders, let’s talk.