50% of first sales hires fail in their first year. Why? Founders often hire too soon, without a clear sales system. This leads to chaos, wasted time, and missed opportunities. Before you hire, you need to prepare the groundwork to set your first sales rep up for success.
Here’s a quick checklist to follow:
- Define Your Ideal Customer Profile (ICP): Pinpoint your target audience with measurable criteria like industry, size, and buyer role.
- Document Your Sales Process: Break it into clear steps (e.g., Lead > Demo > Close) and create scripts, playbooks, and objection-handling guides.
- Set Metrics: Track both effort (calls, emails) and results (close rates, revenue).
- Hire for Mindset: Look for independent, motivated candidates who can thrive without a big support system.
- Onboard Effectively: Provide a playbook, shadowing schedule, and 30/60/90-day goals to get them up to speed.
Skipping these steps risks failure. With preparation, you’ll build a repeatable system that scales. Chaos doesn’t scale – systems do.
First Sales Hire Preparation Checklist for Solo Founders
Pre-Hire Checklist: What to Build Before You Post the Job
Before you post a job listing, it’s crucial to prepare the tools and processes your new hire will need from day one. This doesn’t mean creating a flawless system – it’s about documenting what already works so that someone else can follow it. Without a clear, written process, your new hire might spend weeks guessing instead of driving results. Laying this groundwork allows your sales hire to get up to speed quickly.
Document Your Ideal Customer Profile
Start by clearly defining your target customer with five to seven measurable criteria, such as industry, company size, location, and buyer role. For example, you might target companies in the tech sector with 50–200 employees, based in the U.S., and selling to a VP of Engineering or a Director of Operations. Additionally, note key details like your typical deal size (Annual Contract Value), the expected ROI for customers, and the average length of your sales cycle.
Go deeper by identifying behavioral triggers and pain points. What events make a prospect seek your solution? These could include a failed product launch, a looming compliance deadline, or securing a new round of funding. It’s also important to differentiate between the end-user and the economic buyer, as their priorities often differ in enterprise sales. To make this even more actionable, create a "day in the life" document outlining your customer’s daily workflows, industry-specific language, and current processes. Don’t forget to include common objections you’ve faced during founder-led sales, along with the exact responses that worked.
"Before hiring your first salesperson, you don’t need to have the exact recipe made yet. But you should have most of the ingredients in the cupboard." – Meka Asonye, Partner, First Round Capital
Map Your Sales Process
Break your sales process into five to seven clear steps, from lead to close. A simple pipeline might look like this: Lead > Contacted > Demo > Proposal > Negotiation > Closed. Define what qualifies a lead at each stage and establish a follow-up schedule. For example, you might require contacting leads within 24 hours, following up within 48 hours of a demo, and sending proposals within a week.
Your sales process should include a documented pitch, demo script, and pricing model – something your new hire can easily pick up and execute. Without this, the transition from founder-led sales can be difficult. Kyle Parrish, Figma’s first sales hire, joined when the company had $2M ARR and around 40 employees. Because there were no notes or documentation on prior deals (even major ones like Microsoft), the process was far more challenging than it needed to be. Avoid this pitfall by creating a playbook of common objections and proven responses.
Set Up Metrics and CRM
Once your process is documented, shift your focus to measurable performance metrics. Track both activity metrics (like calls made, emails sent, and demos booked) and outcome metrics (such as close rates, deal size, and quota attainment). Activity metrics measure effort, while outcome metrics gauge results. Early on, evaluate your hire not just on pipeline volume but also on their ability to provide valuable market feedback and insights.
Make sure your CRM is configured with your pipeline stages and basic reporting before your hire’s first day. This ensures data entry starts immediately and sets the tone for good CRM practices. In enterprise sales, a win rate of 35% is impressive, so your CRM should monitor conversion rates at each stage to identify bottlenecks. Set a clear scaling milestone – like achieving 10 Sales Qualified Leads per month with a 25% discovery-to-demo conversion rate for two consecutive months – before bringing on a second rep.
| Metric Category | What to Track | Purpose |
|---|---|---|
| Activity (Leading) | Calls made, emails sent, demos booked | Measures effort and daily execution |
| Conversion (Process) | Lead-to-SQL, Discovery-to-Demo, Win rate | Highlights bottlenecks in the sales process |
| Outcome (Lagging) | Revenue generated, quota attainment, average deal size | Tracks overall performance and ROI |
Hiring Checklist: What to Look for in Candidates
When making your first sales hire, you need someone who thrives in the unpredictable environment of an early-stage company. Many hiring missteps happen because businesses bring on candidates suited for a different stage of growth. At this point, you need someone who can operate independently, executing your system without relying on a large support team.
Once you’ve established your pre-hire system, the next step is finding a candidate who can work effectively within it.
Screen for Mindset First
Start by looking for missionaries, not mercenaries. A missionary is driven by building something meaningful and cares about equity and the company’s long-term success. A mercenary? They’re mostly interested in the commission structure and hitting quotas. During interviews, try an "anti-sell" approach – be upfront about the challenges, like limited resources, frequent rejection, and the need for hands-on work. Pay attention to their response.
To assess coachability, use the "re-do" exercise. After a mock pitch, give them direct, critical feedback and ask them to immediately redo part of the pitch. This will show you how quickly they learn and whether they can take feedback without letting their ego get in the way. Look for candidates who can admit weaknesses and adapt in real time. Avoid those who get defensive or resist constructive criticism.
"I’d rather hire the salesperson from the second-best company rather than the first – that person probably had a 10x harder time than the person who was selling the category winner." – Eric Lasker, CRO of Varda Space
Once you’ve confirmed their mindset, make sure their experience matches your sales cycle and deal size.
Match Experience to Your Deal Size
Focus on candidates who have experience closing similar deal sizes and managing the entire sales process – from prospecting to closing. For instance, if your average deal size is $25,000, don’t hire someone who’s only closed $500,000 enterprise contracts with a team of sales engineers and legal experts doing the heavy lifting. They’ll likely struggle with the hands-on tasks required at your stage, where they’ll need to handle every step themselves.
Be cautious of candidates from massive companies like Salesforce or Oracle, often referred to as "logo dragons." These individuals may be accustomed to working with established brand recognition, inbound leads, and a robust support infrastructure – none of which are typical in an early-stage environment. For example, Zander Steele, who served as the first sales hire at Hyperscience between 2017 and 2021, helped grow the company from $1M to $30M in ARR because he was comfortable building processes from scratch rather than relying on a playbook from a large corporation.
Test Skills During Interviews
Put candidates to the test by giving them 48 hours to learn your product from basic notes and deliver a pitch. This will reveal how quickly they can ramp up and adapt to a new system. Keep instructions minimal to see if they ask clarifying questions.
You can also assign a written take-home task, such as drafting an outbound email to a real prospect or outlining a "week one" plan. This could include which accounts they’d target and how they’d structure early sales reporting. These tasks help you evaluate their attention to detail and their ability to communicate complex ideas clearly – without relying on a marketing team to do the heavy lifting. Use a standardized scorecard to grade candidates across areas like scrappiness, coachability, and process-oriented thinking. Don’t let charm or charisma sway your judgment.
This structured approach ensures you’re thoroughly evaluating each candidate, checking off every box on your hiring checklist.
| Trait | Why It Matters | Red Flag |
|---|---|---|
| Grit | Can handle constant rejection while staying motivated | Relies on leads from an SDR team |
| Missionary Mindset | Committed to long-term growth and building from the ground up | Focuses only on commission structure and quotas |
| Scrappiness | Can create their own materials, like decks and emails | Asks, "When will the sales deck be ready?" |
| Technical Savvy | Can demo the product and collaborate with engineers | Depends heavily on technical staff for basic product questions |
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Onboarding Checklist: First 30 Days Setup
Once you’ve nailed down your processes and selected the right candidate, the next step is making sure your new hire gets up to speed during their first 30 days. A structured onboarding process is key to helping them adopt a system they can execute independently. The goal? Transfer your expertise into a repeatable, efficient workflow they can follow without needing constant guidance.
Here’s how to break down the onboarding process into three actionable steps for maximum impact.
Create a Written Playbook
Start by preparing a straightforward reference guide for your new hire. This document should include the essentials:
- A transcribed demo script to serve as a baseline.
- Your Ideal Customer Profile (ICP) with 5–7 clear criteria – steer clear of vague descriptions like "anyone with a budget."
- A list of common objections paired with approved responses.
- A detailed breakdown of your pricing model, including value justifications.
- A "day in the life" overview of your typical customer to highlight their triggers and buying behavior.
This doesn’t need to be fancy – a simple Google Doc will do the trick. For example, one telecom company boosted quota attainment by 20% just by introducing structured onboarding documentation.
Build a Shadowing Schedule
Use a "watch, then do" approach to develop early skills and reinforce the playbook. In the first week, have your new hire shadow 5–10 calls to observe pacing, discovery questions, and how objections are handled. By week two, they should start leading calls while you listen in and provide immediate feedback. Record these sessions for later review.
To test their understanding, have them complete a "week one demo" by the end of their first week. This ensures they’ve grasped your value proposition before engaging with real prospects. Begin with low-stakes accounts, like following up on lost opportunities or smaller deals, to help them build confidence without jeopardizing major revenue.
Set 30/60/90 Day Goals
Clear milestones are essential for tracking progress. Here’s a breakdown:
- Days 1–30: Focus on learning. Have them listen to 10–20 past call recordings in your CRM, interview 2–3 customers to gather insights, and set up all necessary sales tools.
- Days 31–60: Transition to execution. During this phase, they should build a target list of 50–100 accounts based on your ICP, start outreach to warm leads, and manage follow-ups on open deals.
- Days 61–90: Prioritize performance. Set measurable targets, like generating 10 Sales Qualified Leads per month and achieving a 25% discovery-to-demo conversion rate. Schedule weekly one-on-ones to review call recordings and address any performance gaps.
"Grade on learnings, not pipeline (at first)." – Meka Asonye, Partner, First Round Capital
It’s worth noting that about 50% of first sales hires don’t make it past their first year – not because they lack talent, but because of poor onboarding. By following these steps, you’ll give your new hire the tools they need to succeed, freeing you up to focus on closing high-value deals and scaling your business.
Conclusion: Use This Checklist or Risk Failure
While this checklist won’t promise success, ignoring it almost guarantees failure. Skipping these steps is often why nearly half of first hires fall short – not because they lack talent, but because the groundwork wasn’t laid. For more practical strategies to refine your sales process with AI, subscribe to our AI Acceleration Newsletter.
A bad hire doesn’t just cost time and money – it can push potential customers toward your competitors and create unnecessary management headaches, pulling your focus away from growing your business.
Before you post that job listing, make sure you’ve got these bases covered: identify your Ideal Customer Profile, outline your sales process, set up your CRM, and define the metrics that matter most. Prioritize hiring for mindset over experience, and set your new hire up for success with a clear playbook and well-defined 30/60/90-day goals.
Preparation is what separates a scalable, efficient system from the chaos of founder-led operations. By putting solid systems in place now, you’ll avoid costly mistakes down the road and turn uncertainty into a repeatable, reliable process.
Chaos doesn’t scale – systems do. For more proven strategies, join us at our next Founders Meeting. Small group, limited availability. https://maccelerator.la/en/live-presentation/
FAQs
How can I clearly define my Ideal Customer Profile (ICP) before hiring my first sales rep?
Start by diving into your current customer data. Create a spreadsheet that includes key details like company size, industry, location, revenue, and the specific problem your product helped solve. This will help you spot patterns among your most successful customers and identify shared characteristics.
From there, define firmographic criteria such as company annual recurring revenue (ARR) (e.g., $5M–$50M), employee count (50–200), and industry focus (like SaaS or FinTech). Add technographic details, such as whether they use Salesforce, and buying-process signals like decision-maker roles and budget cycles. To make your ideal customer profile (ICP) practical, use a simple qualification framework like BANT – which stands for Budget, Authority, Need, and Timeline.
Summarize all this information in a one-page checklist with clear yes/no criteria. Test it out with a few warm leads to ensure it’s realistic and effective before moving forward. A well-defined ICP gives new hires a clear direction right from the start, cutting down on guesswork and driving better early outcomes.
What should I prioritize when hiring my first sales rep as a solo founder?
When bringing on your first sales rep, focus on finding someone who thrives in uncertain, early-stage environments – someone who’s comfortable navigating situations without a clear roadmap. It’s essential to choose a candidate who can stick to an established sales process rather than attempting to overhaul it from the start. Being coachable is another must-have trait; look for individuals who value feedback and teamwork over personal ego. Lastly, make sure they bring relevant experience to the table, whether that’s familiarity with your industry, handling deals of a similar scale, or working with your target customers.
What’s the best way to onboard my first sales hire as a solo founder?
To bring your first sales hire on board successfully, it’s all about having a clear, organized plan that gives them the tools and guidance they need from day one. Start by creating a concise, one-page sales playbook. This should include your Ideal Customer Profile (ICP), a breakdown of your sales process, and a follow-up schedule. Make sure they have access to everything they’ll need – like your CRM, email accounts, and pre-made templates – before their first day.
In their first week, focus on hands-on learning. Arrange shadowing sessions where they can listen in on your calls and demos to pick up on tone, objection handling, and overall flow. Pair this with short, practical training sessions on key skills like lead qualification, follow-ups, and delivering demos. By the end of the week, they should start making outbound calls, but with your guidance.
Set clear performance goals for their first 30, 60, and 90 days. These could include metrics like the number of calls made, demos scheduled, or deals closed. Meet weekly to review their progress, troubleshoot any challenges, and fine-tune their approach. A well-structured onboarding process not only reduces confusion but also helps your new hire hit the ground running and perform effectively in record time.
