Here’s a significant investment that goes into finding great commercial talent. Whether you’ve engaged a recruitment company or invested your own time in finding the right person, the process doesn’t end once you’ve made the hire. In fact, that’s exactly when the real work begins. 

Most salespeople leave their roles not because they aren’t good enough, but because they weren’t set up for success from day one. I’ve seen this myself as both a hiring manager and as a “founding sales hire” joining early-stage companies. 

Proper onboarding is absolutely critical 

Transitioning from founder-led sales to having dedicated commercial talent isn’t easy. But the investment you make in the first 30-60 days will pay off later.  

The failure rate when hiring salespeople can be alarmingly high, but as a founder, you can mitigate many of these risks by taking a structured approach to onboarding. 

Setting the right expectations 

One of the most common pitfalls I see is misaligned expectations. Sometimes founders have unrealistic timelines, expecting new commercial hires to generate significant ARR within just three months. This simply isn’t realistic. 

If expectations aren’t clearly aligned, your salesperson could be doing excellent work like creating pipeline, refining messaging, and building relationships, but if you are expecting immediate transactional results, you’ll start to think it’s not working. 

It’s essential to have realistic expectations that align with your new hire’s understanding. While this should have been discussed during the interview process, it’s worth revisiting when they come on board. Be explicit about what you expect in the first three, six, and twelve months. 

Measuring onboarding success 

During the onboarding period, revenue shouldn’t be your primary metric. Instead, focus on the activities and competencies that will ultimately lead to revenue generation. 

Consider implementing a structured weekly approach: 

• End of week one: Ask your new sales hire to deliver a 3-4 minute elevator pitch on your company. 
• End of week two: Have them create one or two personalised prospecting emails that show how they’d approach potential clients. 
• End of week three: Request a demo of your product. 
• End of week four: Ask them to present a prospecting strategy that outlines how they’ll approach the market. 

These milestone tasks serve multiple purposes. They give your new hire clear objectives to work toward independently, reducing the need for constant supervision. They also provide structured deliverables that build toward full onboarding, while giving you valuable insight into how they process information and apply it. 

Avoid information overload 

One of the biggest mistakes founders make is overwhelming new hires with too much information at once. I’ve seen founders pull out a 57-page slide deck covering everything from company vision and mission to case studies and competitive analysis, then attempt to cover it all in a three-hour session. But it’s counterproductive.  

The reality is that your new hire will only absorb a fraction of that information. Instead, break your onboarding into digestible, focused one-hour sessions: 

• A dedicated session on competitors 
• A focused block on CRM hygiene 
• A specific slot on the sales process 
• A targeted session on company vision with the founder 
• A comprehensive product demo with the CTO 

This sectioned approach allows for questions, encourages deeper understanding, and gives your new hire time to process information between sessions. I’ve been there myself and and can tell you that it’s far more effective than dumping everything at once. 

Structured onboarding plans 

Ideally, you should have a V1 sales playbook documented before your new hire arrives – even if it’s just a 3-4 page Word document. This playbook helps form the foundation of your onboarding plan, as the two are intrinsically linked. 

If you have something documented, you can provide your new hire with a manual they can reference. At a minimum, your playbook should cover: 

• Company vision 
• Value proposition 
• Competitive landscape 
• Pricing structure 
• Partner ecosystem 
• Marketing strategy 
• Customer case studies 

Break these topics into approximately 30 sessions spread over a month to avoid overwhelming your new hire. Aim for two to three scheduled sessions per day, with additional time for independent work. 

Balance the learning 

The most effective onboarding combines structured sessions with independent work. For example: 

• Ask your new hire to conduct a SWOT analysis on five competitors 
• Have them review your current email messaging and identify potential improvements 
• Request they research industry trends relevant to your solution 

These activities encourage critical thinking and help them engage with your systems and processes. They also give you insight into how they absorb and apply information, allowing you to adjust your onboarding as needed. 

Tailoring onboarding to different commercial roles 

While there’s significant overlap, onboarding should be tailored to the specific commercial role: 

SDRs  

For SDRs focused primarily on outbound prospecting, strip down the information to what they absolutely need: 

• USPs and value proposition 
• Case studies 
• Market differentiation 
• Ideal Customer Profile (ICP) 
• Target personas 

While they should receive a product demo, they don’t need the same depth of knowledge as an account executive. SDRs need enough information to sell a meeting, not close a deal. 

Account Executives 

Account executives need the full breadth of information, including: 

• Detailed product knowledge 
• Pricing and packaging options 
• Sales process methodology 
• Negotiation parameters 
• Implementation and success metrics 

Revenue Leaders 

Revenue leaders require everything an account executive does, plus: 

• Current team makeup and dynamics 
• Existing go-to-market plans and strategy 
• Growth expectations and targets 

Common onboarding mistakes to avoid 

1. Not having an onboarding plan at all. Many founders simply expect salespeople to “figure it out” or “go sell some shit.” This approach fails a lot more than it succeeds. 
2. Information dumping without structure. The first day is a high-level meet-and-greet, and by Tuesday you’ve blocked out four hours to dump all information at once. This overwhelms rather than empowers. 
3. Failing to set clear expectations. Without defined timeframes and success metrics, both you and your new hire will become increasingly anxious as weeks pass without clarity on what “good” looks like. 
4. Not defining success metrics for both onboarding and ramping. Remember that a new salesperson goes through two distinct phases: onboarding and ramping (with reduced targets). You’re likely looking at five months before they’re fully productive, and if success metrics aren’t clearly defined from the beginning, you may get itchy feet after four months. 

The real impact of proper onboarding 

I’ve seen numerous cases where salespeople are only partially onboarded before being thrown into the deep end. A big prospect meeting comes up, and suddenly onboarding is scrapped in favour of immediate action. The founder thinks, “Why don’t you take this one, new salesperson? You know more about sales than me – I’m just a technical founder.” 

This approach backfires spectacularly. Your new hire may have sales skills, but they don’t yet know your industry, stakeholders, or value proposition well enough to be truly effective. Without proper onboarding, they’ll miss opportunities and leave business on the table, attempting to wing it with sales ability alone – which simply doesn’t work. 

The investment required isn’t enormous. Even if you dedicate just 30 hours across the first 30 days (1 hour per day) you’ll set your commercial hire up for success. If you can’t invest that minimal time, you probably shouldn’t be hiring at all. This is people’s livelihood you’re dealing with, and it’s your duty to invest the time. 

Founders often tell me, “I don’t have time because we’re building this new feature,” or “There’s never a good time.” But by blocking out just one or two hours daily for the first 30 days, you’ll see exponential returns within six months.  

The difference between a properly onboarded commercial hire and one who was left to figure things out is immense. 

Conclusion 

The investment you make in properly onboarding your commercial hires directly impacts your company’s revenue trajectory.  

Skip this crucial step, and you’re effectively wasting the significant resources you’ve already invested in recruitment. 

 Simply, take the time to create a structured onboarding plan, set realistic expectations, and measure the right metrics during the first few months.  

Author: Matthew Codd

I’m Matthew, I have 15 years of commercial leadership experience, helping VC-backed B2B technology companies scale revenue and transition from founder-led sales.  

I use my experience to help early-stage start-ups with GTM expertise, sales best practice, and hiring insights.  

I co-founded Cosmic Partners in 2022. We are SaaS sales recruitment specialists for VC backed B2B tech companies.