Introduction
Usually, the conversation of making your first sales hire happens when you've hit the wall. Your pipeline is full, but you’re stretched in 10 different directions, and you can't close fast enough. Or you're turning away leads because you don't have the bandwidth. Maybe you're already working 80-hour weeks, and following up with leads feels like a second job.
You need a sales rep.
So you post a job on Indeed. Fifty resumes land in your inbox. Half are spam. The other half looks identical: "Dynamic, results-driven sales professional with a proven track record of exceeding quota."
But that’s probably written by AI, and let’s be honest, what does “dynamic” even really mean?
You interview 10 candidates. They all say the right things. You hire the one with the best energy. Three months later, they've closed zero deals and you're back to square one - except now you're out $30K in salary, $2500 in tools, wasted an entire quarter, and worked 100 hours a week instead of 80.
In this article, we’ll walk you through: how to find, interview, and onboard commercial services sales reps who actually perform. You'll get a job description template, interview questions that reveal fit (not just charisma), a scorecard for evaluating candidates, and a 30/60/90-day onboarding plan that cuts ramp time in half.
If you're a hiring manager or CEO bringing on your first sales role—or rebuilding after a bad hire—this is your blueprint.
Why Hiring Your First Sales Rep Is Different (and Harder)
Hiring your first sales rep is not like hiring your fifth one. When you're at five reps, you've got a playbook. You know what “good” looks like, and you can pair the new hire with a top performer for shadowing.
But when you're hiring your first rep, you're building the machine from scratch.
Here's the tension: You need someone who can sell, but you also need someone who can figure things out. Most experienced sales reps are used to structured CRM workflows, email automation, documented processes, established territories, and warm leads from marketing.
You don't have any of that yet. You need a rep who's comfortable with ambiguity and willing to build while they sell. That's a rare combo.
Most great salespeople want to walk into a system that already works. They don't want to be the guinea pig. So you're faced with a choice:
Hire experience (someone who's sold in your industry, knows the objections, has a Rolodex) - but risk they can't adapt to a less structured environment.
Hire potential (someone scrappy, hungry, coachable, but unproven) - and risk they can't close (at least in their first quarter).
The right answer? Wish I could give you that, but I can’t.
But I can give you some tips, a few things to keep in mind, and all the resources you’ll need to make a great hire.
If you're in a well-defined market (commercial HVAC in a major metro), hire for experience. The playbook already exists. You just need someone to execute it.
If you're in a new or complex market (selling a new service model or entering an underserved vertical), hire potential. You need someone who can experiment, learn fast, and not panic when the first 20 calls go absolutely nowhere.
I know this will sound like a broken record, but most founders hire for charisma. They meet a candidate who's confident, articulate, enthusiastic (and looks a bit like us when we started our career), and assume that translates to results.
It doesn't.
Charisma gets you in the door. Discipline closes deals.
Your goal is to find a rep who ramps in 90 days (or less), hits quota by month four, and becomes the template for your next five hires.
Let's build the process that gets you there.
The 5-Step Hiring Process for Commercial Services Sales Reps
Most hiring processes are too long (candidates drop out) or too short (you miss red flags). Here's the balance: five to seven steps, 3-4 weeks start to finish.
Step 1: Define the Role (Before You Post Anything)
Don't write a job description until you can answer these:
What will this person actually do? (Prospecting? Closing? Both?)
What's their territory? (Geographic? Vertical? Account size?)
What's their quota? (Revenue target, deal count, activity metrics?)
What tools will they use? (CRM, prospecting software, proposal tools?)
Who will they report to?
What's success in 30/60/90 days?
If you can't answer these, you're not ready to hire. You'll attract the wrong candidates and have no way to measure performance.
Step 2: Write the Job Description
A good job description does two things: attracts the right candidates and repels the wrong ones.
Most job postings read like fiction: "Join a fast-growing, innovative company disrupting the HVAC industry!" That tells the candidate nothing.
A better version: "We're a 10-person commercial HVAC company serving hospitals and office buildings in Dallas. You'll be our second sales rep. Your job is to prospect 50 accounts per week, book discovery calls, close deals, and help us build the sales playbook. First-year OTE: $80K–$100K. You'll be in the field 3 days a week."
That's specific. Candidates know exactly what they're signing up for.
Step 3: Source Candidates
Post the job, but don't stop there. The best candidates aren't actively looking - they're already employed.
Where to look:
Industry peers (who's selling for your competitors?)
Adjacent verticals (commercial solar, roofing, or building automation systems reps make great HVAC reps; they all sell to facilities managers)
Former field workers (ex-HVAC techs, electricians, roofers - they know the product and the objections)
Referrals (ask every customer, vendor, and partner)
Step 4: Screen & Interview
Phone screen (20 minutes): Confirm the basics - availability, comp expectations, location, work style. If they pass, move to the first interview.
First interview (45 minutes, video): Behavioral questions. How do they handle rejection? How do they prioritize? How do they learn? (We'll cover the exact questions in Section 5.)
Second interview (60 minutes, in-person): Role-play. Give them a scenario: "You're calling a facilities manager at a hospital. They've been using a competitor for 10 years. Walk me through the first call."
Listen for structure, questions, and how they handle objections. This is where you'll see if they can actually sell—or if they're just good at interviewing.
Half-day ride-along (4 hours, in the field): Take them with you on 2-3 sales calls or site visits. Let them observe how you handle discovery, objections, and closing.
Why this matters: You'll see how they interact with prospects in real time, read the room, and ask good follow-up questions. If they sit quietly in the truck and don't engage, that's a red flag. Great reps are curious - they'll ask you what worked, what didn't, and why you made certain calls.
Reference checks: Call their last two managers. Ask one question: "Would you hire them again?"
If they hesitate, dig deeper—not for dirt, but to understand why. If there’s a long pause… You probably have your answer.
Step 5: Make the Offer
Don't lowball. Don't oversell. Be honest about the role, the ramp, and the upside.
Include: Base salary, commission structure, quota, benefits, start date, and onboarding plan.
Give them 48–72 hours to decide. If they need longer, they're not that excited.
Where to Find Commercial Sales Talent (Ranked by Quality)
Not all sourcing channels are created equal. Some give you high-quality candidates who stick around. Others flood your inbox with resumes that waste your time.
Here's where to look, ranked from best to worst.
Tier 1: Referrals from Your Network
Quality: Highest | Speed: Slow | Cost: Free (or a referral bonus)
Ask every customer, vendor, partner, and industry contact: "Do you know anyone great at sales who's looking for their next opportunity?"
Referrals come pre-vetted. They're more likely to fit your culture, understand your market, and stick around longer than a cold hire from Indeed.
Pro tip: Offer a referral bonus ($500–$1,000) to employees or customers who send you a hire. People are more motivated to think hard about who they know when there's something in it for them.
Tier 2: Poaching from Competitors or Adjacent Verticals
Quality: High | Speed: Medium | Cost: Time (outreach, recruiting)
Who's selling for your competitors? Who's crushing it in adjacent markets (commercial cleaning, fire/life/safety, electrical, or BAS)?
Reach out directly on LinkedIn. Be transparent: "We're hiring. Here's why you should consider us."
Tier 3: Industry Job Boards (Indeed, LinkedIn, ZipRecruiter)
Quality: Medium | Speed: Fast | Cost: $200–$500 per post
You'll get volume, but you'll also get noise. Expect 50–100 applicants, and half won't even read the job description - these can be eliminated quickly with a few key questions.
Pro tip: Use screening questions to filter out unqualified candidates before they hit your inbox. Examples: "Do you have experience selling to facilities managers or property managers? Yes/No." "What's your current base + commission?"
Tier 4: Recruiting Agencies
Quality: Medium (depends on the agency) | Speed: Fast | Cost: 15–25% of first-year salary
Agencies can save you time, but they're expensive - and you're gambling on whether they actually understand your market.
Only worth it if you're hiring multiple reps at once, or if you need someone ASAP and don't have the bandwidth to source yourself.
Pro tip: Use contingency agencies (you only pay if you hire) instead of retained search (you pay upfront, whether they deliver or not). The candidates they choose may not be a good fit, but at least you’re not paying out of pocket to source applicants.
Tier 5: Cold Outreach on LinkedIn
Quality: Low to Medium | Speed: Slow | Cost: Time
If you have an office manager or an assistant, sending LinkedIn messages can be a surprisingly effective (and free) way to get applicants in front of you.
Search for "commercial sales rep" or "field sales" in your city. Message 20–30 people with something simple: "Hey [Name], I saw you're in commercial sales in [City]. We're hiring for a role at [Company]. Interested in learning more?"
Response rate: 5–10%. Most won't reply, and the ones who do are either actively job-hunting (which may or may not be a red flag, depending on why they're looking) or casually curious.
But here's the thing—you can quickly filter people based solely on their responses. If the first thing they ask is "What's the salary?" without any questions about the role, the company, or what success looks like, that tells you something. If they ask thoughtful questions about territory, quota, tools, and support, that tells you something else.
Be mindful of what their reply says about their motives.
Pro tip: Look for people who've been in their current role for 2-3 years and seem to be performing well (check for promotions, recommendations, or activity). They're stable enough not to be a flight risk, but might be ready for their next opportunity.
Tier 6: "Instant Apply" Platforms or Mass Job Boards
Quality: Low | Speed: Fast | Cost: $50–$200
You'll get hundreds of applicants. 90% will be unqualified. Unless you have an HR team to screen them, skip this entirely. It's not worth the time or the noise.
Job Description Template (Fill-in-the-Blank)
If you don’t already have one written, you can use this template to write a job description that attracts the right candidates and repels the wrong ones.
Job Title: [Field Sales Rep | Inside Sales Rep | Account Executive]
Location: [City, State—be specific. Remote? Hybrid? Field-based?]
About Us: [2–3 sentences. What do you do? Who do you serve? How big is the team?]
Example: "We're a 12-person commercial HVAC company serving hospitals, office buildings, and multifamily properties in Phoenix. We've been in business for 8 years and are growing 30% year-over-year."
The Role: You'll be responsible for [prospecting new accounts | closing inbound leads | managing a territory]. Your goal is to [hit $X in revenue | close X deals per month].
Day-to-Day:
Prospect 50+ accounts per week via [phone | email | in-person]
Book and run discovery calls with [facilities managers | property managers]
Deliver proposals and close deals
Manage your pipeline in [Salesforce | HubSpot]
Collaborate with [operations | account management] to hand off new customers
What We're Looking For:
[X years] of experience selling [B2B services | to commercial properties]
Comfortable with [cold calling | field sales | consultative selling]
Self-starter who can work independently
Coachable and open to feedback
Based in [City] or willing to relocate
Nice to Have:
Experience using [CRM name]/[Prospecting Tools]
Existing relationships with [facilities managers | property managers]
Background in [HVAC | construction | trades]
Compensation:
Base: $[X]
Commission: $[Y] (OTE: $[X+Y])
Quota: $[Z] per [month | quarter]
Benefits: [Health insurance | PTO | car allowance]
To Apply: Send your resume and a 2–3 sentence note on why you're interested to [email]. No cover letters. No calls.
Post it on LinkedIn, on your website, and send it to your network. A simple job description like this can drive a ton of great candidates to your inbox.
Sales Interview Questions That Actually Reveal Fit
Most interview questions are useless. "What's your greatest strength or weakness?" tells you nothing except how well someone can rehearse a canned answer.
Here are questions that reveal how a candidate actually works - and whether they'll succeed in your environment.
Category 1: Discipline & Work Ethic
"Walk me through a typical day. What time do you start? What's the first thing you do?"
What you're listening for: Structure. Do they have discipline and a routine, or do they wing it every day? Great reps have systems. Weak reps just "show up and see what happens."
"How many calls did you make last week? How many emails? How many meetings did you book?"
What you're listening for: Specificity. If they can't give you numbers, they don't track their activity. And if they don't track it, they can't improve it. Red flag.
Category 2: Handling Rejection
"Tell me about a time you got rejected 10 times in a row. How did you handle it?"
What you're listening for: Resilience. Do they take it personally and spiral? Or do they treat it as part of the job and move on to the next call?
Commercial sales is all about how you handle rejection. If they can't handle hearing "no" without getting demoralized, they won't last.
"What's the longest sales cycle you've ever worked? How did you stay engaged with the prospect over that period?"
What you're listening for: Patience and persistence. Commercial cycles are long (60–90 days, sometimes longer). Can they stay organized and keep deals warm without forgetting about them or smothering the prospect?
Category 3: Learning & Coachability
"Tell me about a time a manager gave you tough feedback. How did you respond?"
What you're listening for: Defensiveness vs. openness. Great reps take feedback, implement it, and come back better. Weak reps argue, make excuses, or nod along but never change.
"What's the last thing you taught yourself? How did you learn it?"
What you're listening for: Curiosity and self-direction. If they're not learning on their own, they won't adapt when the market shifts or when your product changes.
Sales reps who wait to be taught everything don't survive in unstructured or rapidly changing environments.
Category 4: Discovery & Qualification
"Walk me through your discovery process. What questions do you ask? How do you know if someone's a good fit?"
What you're listening for: Structure and intentionality. Do they have a framework (like BANT), or do they just wing it and hope the prospect volunteers information?
"Tell me about a time you disqualified a lead. Why did you walk away?"
What you're listening for: Discipline. Weak reps chase everything. Strong reps know when to say no and move on to better opportunities.
If they can't tell you about a time they walked away from a bad-fit prospect, they probably waste a lot of time on deals that were never going to close.
Category 5: Role-Play (Second Interview Only)
Scenario: "I'm a facilities manager at a 200,000 sq. ft. office building. We've been using the same HVAC company for 10 years. You're calling me cold. Go."
What you're listening for:
Do they research the building first, or do they just pitch blindly?
Do they ask questions, or do they talk at you?
How do they handle the objection: "We're happy with our current provider"?
Do they close for a meeting, or do they try to close the entire deal on the first call? (The latter is a red flag.)
Pro tip: Interrupt them mid-pitch with a curveball objection. "Actually, we just renewed our contract last month. Call me next year."
Do they give up immediately? Or do they reframe and keep the conversation going?
This is where you see whether they can think on their feet—or if they freeze when the script doesn't go as planned.
The Interview Scorecard (How to Evaluate Candidates)
Don't hire based on "vibe." Use a scorecard. Rate every candidate on the same criteria - first, it’s the law in most states, second, you want a solid baseline to measure every rep by, removing “gut feelings” and guesswork.
Here's what to score (1–5 scale):
Relevant Experience (20% weight): Have they sold B2B services? To commercial properties? Do they understand the market and the buyer?
Activity Level (20% weight): Can they cite specific numbers (calls, emails, meetings)? Do they track their own performance?
Resilience (15% weight): How do they handle rejection? Do they quit when things get hard, or do they adjust their approach?
Coachability (15% weight): Do they take feedback well? Are they curious? Do they ask questions or get defensive?
Discovery Skills (10% weight): Do they ask good questions? Can they qualify a prospect, or do they just pitch?
Communication (10% weight): Are they clear and concise? Do they listen, or do they just talk?
Culture Fit (10% weight): Will they thrive in your environment (scrappy vs. structured, independent vs. team-oriented)?
Scoring:
5 = Exceptional (Top 10%)
4 = Strong (Would succeed)
3 = Adequate (Risky)
2 = Weak (Red flags)
1 = Unqualified (No fit)
How to use it: Multiply each score by the weight. Add them up.
Example:
Experience: 4 × 20% = 0.80
Activity: 5 × 20% = 1.00
Resilience: 4 × 15% = 0.60
Coachability: 5 × 15% = 0.75
Discovery: 3 × 10% = 0.30
Communication: 4 × 10% = 0.40
Culture: 4 × 10% = 0.40
Total: 4.25 / 5.0
Hiring threshold: 3.5 out of 5 or higher. Anything below is a pass.
Pro tip: Have two people interview every candidate and score independently. Average the scores to reduce bias.
Red Flags to Watch For
These are automatic disqualifiers. If you see any of these, walk away.
Red Flag 1: Can't Cite Specific Numbers
You ask: "How many calls did you make last week?" They answer: "Uh, a lot. I was pretty busy."
Why it matters: If they don't track activity, they can't improve it. Sales is a numbers game. No numbers = no discipline.
And if they're not tracking their own numbers now, they likely won't start when they work for you.
Red Flag 2: Blames Everyone Else for Failures
You ask: "Tell me about a time you missed quota." They answer: "My manager gave me a terrible territory. Marketing didn't send leads. The product was overpriced."
Why it matters: Victims don't succeed in sales. Great reps own their results - good and bad.
Yes, sometimes you get dealt a bad hand. But if every failure is someone else's fault, this person will never take responsibility for fixing their own performance.
Red Flag 3: No Questions for You
You ask: "What questions do you have for me?" They say: "Nope, I'm good!"
Why it matters: If they're not curious about the role, the market, or the company, they're not serious. Great candidates ask about quota, ramp time, tools, and support.
Great candidates ask about quota, ramp time, tools, support, what success looks like, and why the last person in this role left (or why the role is new).
If they don't ask anything, they're just looking for any job, not this job.
Red Flag 4: Job-Hopping (Less Than 1 Year per Role)
Their resume shows: 5 jobs in 4 years.
Why it matters: Either they're getting fired, or they quit when things get hard. They won't stick around long enough to ramp.
Exception: Startups that shut down or undergo layoffs due to downsizing are fine. Just be sure to ask deeper questions about the move so you understand why.
Red Flag 5: Can't Explain Why They're Leaving
You ask: "Why are you looking to leave your current role?" They answer: "I just need a change."
Why it matters: Vague answers hide problems. Dig deeper.
Are they being pushed out? Did they stop hitting quota, and are now on a performance plan? Are they running from a toxic manager (fair), or are they the toxic ones?
If they won't give you a straight answer, there's usually a reason.
Red Flag 6: Oversells Themselves
They say: "I'm the best closer you'll ever meet. I've never missed quota. I can sell anything to anyone."
Why it matters: The best reps are confident but grounded. They know their strengths and weaknesses. They can tell you about deals they've lost and what they learned.
Overconfidence usually covers up insecurity. I’ve never met a rep who didn’t miss quota at least once in their career; hell, I’ve missed quota several times.
But overconfidence and lack of awareness will both lead to wasted time and money for you in the future.
Making the Offer (Comp Structure Basics)
Compensation is where most first-time hiring managers screw up. They either lowball (and lose the candidate to a competitor) or overpay (and set a bad precedent for future hires).
Here's how to structure it so you're competitive without breaking the bank.
What to Offer as a Base Salary?
This will vary by city, but a good place to start is to look at ZipRecruiter, Glassdoor, or Indeed, and search for “salary indexes by city.” You can also find these links by “googling” “commercial services sales salary,” or “field sales rep compensation.” These should give you a good idea of what you’ll need to invest based on your location. We’ll start with a baseline for the purposes of this section:
Guideline: $40K–$60K for inside sales, $50K–$70K for field sales (varies by market and experience).
Why it matters: Base salary covers living expenses while they ramp. Too low, and they'll be stressed and desperate (which kills performance). Too high, and they won't be motivated to hustle for commission.
Commission Structure:
Guideline: 5–10% of closed revenue, paid monthly or quarterly.
Example: If they close $50K in deals, they earn $2,500–$5,000 in commission.
Pro tip: Pay commissions on the next check after a deal closes. You want them focused and motivated, and knowing that their check will double next week or in two weeks because of a closed deal will make a huge difference.
Quota:
Guideline: $500K–$1M per year for commercial services (HVAC, roofing, solar). Monthly breakdown: $40K–$80K in closed revenue per month.
Why it matters: Quota should be achievable but challenging. If 70–80% of your reps hit quota, it's set right. If only 30% hit it, it's way too high (and you'll burn through reps fast).
OTE (On-Target Earnings):
Formula: Base + Commission (assuming they hit 100% of quota)
Example:
Base: $60K
Commission at quota: $30K
OTE: $90K
Pro tip: Make sure your OTE is competitive with market rates. Once again, check Glassdoor, Indeed, or industry salary surveys for your region. If you're $10K–$15K below market, you'll lose candidates to better offers - maybe even competitors.
Accelerators (Optional, But Powerful):
What it is: Bonus commission for exceeding quota.
Example: Hit 100% of quota = 10% commission rate. Hit 120% of quota = 15% commission rate on everything above 100%.
Why it matters: Keeps top performers motivated and prevents them from coasting once they hit their number. You want reps thinking, "If I close one more deal, I make an extra $5K this month."
Ramp Period (Non-Negotiable):
What it is: Reduced or waived quota for the first 30–90 days while they are onboarding.
Example:
Month 1: No quota (learning mode)
Month 2: 25-50% of full quota
Month 3: 50-75% of full quota
Month 4+: 100% quota
Why it matters: You want them to learn without financial pressure. If you put them at full quota on Day 1, they'll panic, skip the fundamentals, and burn out (or burn through your prospect list without building relationships).
Give them time to ramp. It pays off in the long run.
Now, we get a lot of pushback when we say that a commercial services sales rep can be onboarded in 90 days or less. And, if you look at industry averages, you’d be justified in feeling that.
Many companies report spending 90, 120, or even 180 days to get a rep fully productive. But we’ve found that a few strategic tools can make all the difference.
We’ll cover those in a moment.
The 30/60/90-Day Onboarding Plan
Most reps fail because of poor onboarding—not because they can't sell. Here's how to set them up for success.
Month 1 (Days 1–30): Learn the Market
Goal: Understand the product, the customer, and the process. No quota.
Week 1:
Day 1: Orientation (company overview, tools, CRM, comp plan)
Day 2: Product training (ride-along with a technician or attend an install)
Days 3–5: Shadow the owner or top performer (listen to calls, attend meetings)
Week 2:
Study the ICP: Who do we sell to? What problems do they have?
Review 10 closed deals (read notes, listen to recordings)
Build a target account list (50 accounts in their territory)
Week 3:
Make practice calls (role-play with manager/owner)
Send first outreach emails (with manager review)
Book first discovery call (manager attends as backup)
Week 4:
Run five discovery calls (manager/owner shadows)
Send first proposal (manager reviews before sending)
Set activity goals for Month 2
Key Metrics:
50 target accounts identified
5 discovery calls completed
1 proposal sent
Month 2 (Days 31–60): Build the Pipeline
Now that they have a good baseline, let’s see what they can do with what they’ve learned.
Goal: Generate activity and begin to fill the pipeline. Quota: 25-50% of the full quota.
Week 5–6:
Prospect 30-50 accounts per week
Book 3–5 discovery calls per week
Send 2–3 proposals
Week 7–8:
Continue prospecting (consistency is key)
Run discovery calls independently (manager reviews notes)
Close first deal (or identify what's blocking it)
Key Metrics:
75-100 accounts prospected
10–15 discovery calls completed
4–6 proposals sent
1 deal closed (or in final negotiation)
Month 3 (Days 61–90): Hit Quota
Goal: Close deals and prove they can carry a full load. Quota: 75% of full quota.
Week 9–12:
Prospect 50 accounts per week
Book 3–5 discovery calls per week
Send 2–3 proposals per week
Close 2–3 deals
Key Metrics:
Pipeline: $200K+ in weighted opportunities
10+ discovery calls per month
75% of quota hit (or clear path to 100% in Month 4)
What Happens If They're Not Hitting Milestones?
After Month 1: If they haven't completed 5 discovery calls, extend onboarding by 2 weeks. They need more reps.
After Month 2: If they haven't sent 4–6 proposals, diagnose the problem. Not prospecting enough? Qualifying poorly? Coach them.
After Month 3: If they're under 50% of quota with no clear pipeline, it's time for a hard conversation. Either they commit to a performance improvement plan, or you part ways.
Pro tip: Weekly 1-on-1s are non-negotiable during onboarding. Review activity metrics, listen to call recordings, and coach in real-time.
Now, you may be thinking, “Sure, this looks great in a playbook, but does it actually work in the field?” - that’s exactly why we built the plan around real-world data, not theory.
We’ve seen it happen again and again across HVAC, roofing, solar, and janitorial teams: when you pair a structured 30/60/90 framework with the right property intelligence and prospecting tools, ramp time collapses.
Real-World Onboarding Example: Comfort Systems USA Southwest
Few examples show this better than Comfort Systems USA Southwest, a leading HVAC company serving Arizona and New Mexico.
Like many commercial services firms, they faced a familiar challenge: new sales reps were taking six to nine months to ramp up. Even strong hires struggled to get fully productive because so much of their early time was spent figuring out who to call and where to start.
Prospecting meant hours of driving from building to building, searching LinkedIn for property managers, and guessing which accounts were worth pursuing. It wasn’t for lack of effort - it was a lack of visibility.
Then the team adopted Convex, using property intelligence to pinpoint high-value buildings with decision-makers actively searching for their services. They could see which properties had recent permits, aging systems, or upcoming projects - and reach the right contacts before competitors ever showed up.
Sales Consultant Joel Martos summed it up best: “I only have to prospect for two to four hours a week, and I know exactly who to go after.”
That shift turned onboarding from a 6+ month grind into a 90-day success story, helping the company more than double in size. Convex didn’t just make prospecting faster - it gave every new hire a clear, data-backed roadmap to early wins.
Common Hiring Mistakes (and How to Avoid Them)
Even with a solid process, hiring can go sideways. Here are the mistakes we see most often - and how to avoid them.
Mistake 1: Hiring for Charisma Instead of Discipline
What it looks like: You interview a candidate who's charming, confident, and articulate. Great energy. You assume they'll crush it. Three months later, they haven't closed a single deal.
Why it happens: Charisma gets attention. Discipline gets results. They're not the same thing.
That candidate who "kills it" in the interview might be great at performing for 45 minutes - but they’re terrible at making 50 cold calls a day when no one's watching.
The fix: Use the scorecard (Section 6). Weight discipline and activity metrics higher than personality. Ask for specific numbers. If they can't give them, move on.
Mistake 2: Skipping the Role-Play
What it looks like: You ask great behavioral questions, but you never actually see them sell. You hire based on their resume and references.
Why it happens: Role-plays feel awkward. You're worried about putting candidates on the spot. But here's the thing—selling is being on the spot. If they can't handle role-play in an interview, they definitely can't handle a real objection from a prospect.
The fix: Make role-play mandatory in the second interview. No exceptions. It's the only way to see how someone actually performs under pressure.
Mistake 3: Overselling the Role
What it looks like: You tell candidates, "We've got tons of inbound leads! You'll be closing deals in Week 1!" Then they show up and realize there are a few referrals trickling in each month, a couple of form fills on the website, and in reality, they have to prospect from scratch.
Why it happens: You're excited about the company and want to attract top talent. But overpromising backfires. Hard.
When reality doesn't match the pitch, the new hire feels lied to. Trust erodes. They start looking for other jobs before they even finish onboarding.
I've been on the other side of this - twice.
First time, a company told me: "We're getting an average of 231 leads per month." (Yes, that's the actual number they gave me.) I was excited and ended up taking the job.
I didn't ask the right questions—like "What percentage of those leads are qualified?" or "How many convert?" or "Can I see the pipeline?"
During onboarding, reality hit. The "231 leads" were cold names in a spreadsheet purchased from a lead broker. Most were unqualified and uninterested. Took me five months to build a pipeline from scratch and finally hit quota.
Second time? Different company, same pitch.
But this time, I asked tons of questions. I wanted to see the data, talk to the reps, and understand what "inbound" actually meant.
Turns out, it was a great company. They were honest about the numbers, the quality, and what the role actually looked like day to day. I ended up spending a few years at that company, and loved it.
The Lesson: if you oversell the role, good candidates will either figure it out in the interview (and walk away) or in the first 30 days (and start looking for the exit) - which is a waste of your time and money.
Mistake 4: Hiring One Rep Instead of Two
What it looks like: You hire one rep. They're your only salesperson. If they fail, you have no pipeline, no one to compare them to, and no safety net.
Why it happens: Budget constraints or fear of overcommitting. You're thinking, "Let me see if this first one works out before I invest in a second."
But here's the problem: one rep in isolation often plateaus - or quits. There's no one to learn from, no one to compete with, and no accountability partner when things get tough.
The fix: If you can afford it, hire two reps at once.
Yes, it doubles your upfront investment. But you also de-risk the hire. One might not work out, but the other probably will. And two reps push each other - they share what's working, hold each other accountable, and create momentum.
If the budget is tight, at least have a plan to hire the second rep within 90 days of the first. Don't leave your first hire out there alone for six months.
Mistake 5: No Onboarding Plan
What it looks like: New rep shows up on Day 1. You hand them a laptop and say, "Here's the CRM. Go sell." Three weeks later, they're floundering and you're frustrated because they're "not getting it."
Why it happens: You're busy running the business. You assume they'll figure it out because they're "experienced."
But even experienced reps need onboarding. They don't know your product, your market, your objections, or your process. Without structure, they'll waste the first 60 days reinventing the wheel (or worse, building bad habits).
The fix: Use the 30/60/90-day plan from Section 9. Schedule it before they start. Block out time for weekly 1-on-1s. Make onboarding a priority, not an afterthought.
Mistake 6: Waiting Too Long to Fire
I have quite a few stories for this - I’m sure you do too, so we’ll let the section speak for itself.
What it looks like: Rep isn't hitting numbers. You give them "one more month" to turn it around. Six months later, they still haven't closed anything meaningful, and you're finally ready to make a change.
Why it happens: You're conflict-averse. Or you're worried about the sunk cost. Or you keep thinking, "Maybe next month will be different."
Trust me, it won't be.
The fix: Set clear milestones in the onboarding plan. If they miss them by 30%, have a direct performance conversation. If they miss by 50%, part ways.
Holding onto a weak performer costs you more than starting over. They're not just underperforming; they’re setting a standard of underperformance that your whole team sees. And, they're taking up a seat that a strong performer could fill. And every month you wait is another month of lost revenue.
Conclusion & Next Steps
Here's what we've covered:
Hiring your first sales rep is different from hiring your fifth. You need someone who can build while they sell - someone with discipline, resilience, and coachability (not just charisma). The 5-step hiring process gives you structure. The interview scorecard removes bias and gut-feel decisions. And the 30/60/90-day onboarding plan cuts ramp time in half.
The difference between teams that scale and teams that stall? A repeatable hiring process and a real commitment to onboarding.
If you're bringing on your first sales role, start here:
Define the role (territory, quota, tools, success metrics)—before you post anything
Write a job description that's specific and honest
Source proactively (referrals, competitors, adjacent verticals)—don't just wait for Indeed applications
Use the scorecard to evaluate every candidate objectively
Build a 30/60/90-day onboarding plan before they start (not after)
And if you want to give your new reps the tools they need to ramp faster and hit quota sooner, like Comfort Systems USA SW’s team did? Schedule a demo to see Convex in action.
We'll show you how Convex helps commercial services reps build a pipeline of high-quality, high-intent leads in less time - so they're closing deals by Month 2 instead of still figuring out who to call.
FAQs
How do you hire a sales rep?
To hire a sales rep, follow a 5-step process: (1) Define the role (territory, quota, tools, success metrics), (2) Write a specific job description that attracts the right candidates, (3) Source proactively through referrals, competitors, and job boards, (4) Screen and interview using behavioral questions and role-play scenarios, and (5) Make an offer with clear comp structure and onboarding plan. Use an interview scorecard to evaluate candidates objectively and avoid hiring for charisma over discipline.
What are good sales interview questions?
Good sales interview questions reveal discipline, resilience, and coachability—not just charisma. Ask: "Walk me through a typical day. What time do you start? When do you prospect?" (tests structure), "How many calls did you make last week?" (tests activity tracking), "Tell me about a time you got rejected 10 times in a row. How did you handle it?" (tests resilience), and "Walk me through your discovery process. What questions do you ask?" (tests qualification skills). Always include a role-play scenario in the second interview to see how they actually sell.
Where do you find sales candidates?
The best sources are: (1) Referrals from your network (highest quality), (2) Poaching from competitors or adjacent verticals (target reps at smaller companies), (3) Industry job boards like Indeed and LinkedIn (high volume, mixed quality), (4) Recruiting agencies (fast but expensive, 15–25% of salary), and (5) Cold outreach on LinkedIn (low response rate but free). Former field workers (HVAC techs, electricians, roofers) often make great sales reps because they know the product and objections.
How long does it take to onboard a sales rep?
A well-structured onboarding plan takes 90 days. Month 1 (no quota): Learn the product, shadow top performers, make practice calls, complete 5 discovery calls, and send 1 proposal. Month 2 (50% quota): Prospect 50 accounts per week, book 3–5 discovery calls weekly, send 2–3 proposals, and close your first deal. Month 3 (75% quota): Continue prospecting, build a $200K+ weighted pipeline, and hit 75% of quota. By Month 4, reps should be at 100% quota. If they're under 50% after Month 3, have a performance conversation or part ways.
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