SaaS Sales Case Study:
How We Grew SaaS Sales Team from 2 to 30 Sales Reps with $500K Annual Quotas

Bonus Material: Complete Go-to-Market Playbook

This strategy will not work for all businesses. 

It is designed for venture-backed, B2B SaaS companies that want to grow rapidly in what is often called “triple triple double double” growth. That’s tripling revenue twice and then doubling it twice. Revenue growth looks something like this: 

  • Year 1: $1M -> $3M
  • Year 2: $3M -> $9M
  • Year 3: $9M -> $18M 
  • Year 4: $18M -> $36M 

This is hard to do. 

ONLY a very small percentage of companies ever achieve this kind of growth. 

This is the exact strategy we used to do it (at least the triple triple double part to $18 million in 3 years). 

If you want to hire a 20 person B2B SaaS sales team with an average annual quota of $500K and a 10 person SDR team, than THIS is the sales strategy to do it. 

You can skip ahead by downloading the entire VP of Sales Playbook here. Otherwise, I will cover: 

  • Who this works for
  • Early mistakes we made
  • Consequences of getting it wrong
  • How we fed the sales team with leads
  • How to forecast sales headcount
  • How to recruit the best sales reps
  • How to interview and hire sales reps
  • How to onboard and train sales reps
  • How to set your operating cadence

The B2B SaaS Sales Strategy Designed for a Product-Led Growth (PLG) Company

Nowadays, the term PLG is hot. But it seems, so many CEOs and senior go-to-market leaders don’t fully understand the distinction between the two. 

And…don’t fully understand how hard it is to go from one strategy to the other. If you are sales-led, simply adding a free trial to your product, doesn’t suddenly make you product-led. And vice versa. If you are product-led, hiring a bunch of sales reps doesn’t necessarily generate you more revenue.

We started out as a product-led company with a free forever product. From the beginning, we invested heavily in a self-service, user onboarding experience. We designed pathways within the product for users to upgrade to premium plans using their credit card. We executed an entire go-to-market strategy designed to acquire the end user. Get them on our free plan and then self-upgrade to paid plans.  

Overtime, our end users championed our product up to their bosses. Their bosses would then reach out to our company to purchase for their team. 

This is what initially drove the need to hire a sales team. Someone had to talk to the management / leadership stakeholders to help them purchase licenses for entire teams and then help onboard those teams.  

Nevertheless, many of the sales principles and lessons learned from my journey still apply to companies that start as sales-led rather than product-led. 

We Made 3 Major Mistakes That Cost Us Millions in Wasted Venture Capital Dollars

Forecasting, recruiting, hiring, onboarding, training… are all important factors for building a successful sales org. 

And it turns out, it’s not that hard to do any of them. 

HOWEVER, it is hard to be GOOD at them. That’s where CEOs and founders get tricked into hiring the wrong VP of Sales. 

Most sales executives have a lot of confidence. You have to.

They can “talk the talk”. They can articulate a plan. They can explain the steps in that plan. 

However, when it comes down to the tactical execution of that plan, they miss big. And sadly, they burn through a ton of capital in the process. 

Here are the top 3 biggest mistakes we made over the years:

  1. We Forecasted Headcount by Dividing Target New Business Revenue By Sales Rep Quota to Get How Many Reps to Hire
  2. We Paid Account Executives (AEs, quota carrying sales reps) for Any Growth on New Business Accounts They Closed in the First 12 Months
  3. We Hired Too Fast and Too Inexperienced for What Was Required to Do the Job

As a result of making these mistakes, here’s what happened. 

We…

  • experienced lower sales rep productivity
  • Saw sales rep morale decline
  • Had reps fighting over leads and territories
  • Squandered good leads on inexperienced reps
  • Delivered a poor and inconsistent customer experiences 

I could write full articles on all 3 of those mistakes, but for now I want to continue with explaining how we figured out a better way to grow and how you can avoid these mistakes. 

How We Routed 100 Warm Leads to Each Sales Rep Every Month

Ask any marketer how to generate leads for your B2B sales team and they’ll tell you: 

  1. Spend money on Google ads
  2. Spend money on Facebook ads
  3. Drive traffic to content downloads
  4. Send sales the content download leads 

That’s an old strategy that doesn’t really work in 2024. Hell, it didn’t work that well back in 2014 either. 

Sure, Google ads and Facebook ads may play into the overall strategy, but there’s much more to it than that. I explain how we did it in our B2B SaaS Marketing Case Study. 

It breaks down exactly "How We Generated 500K Monthly Visitors, 15K Monthly Trials and $40K of New MRR". 

That strategy fed our sales team with 100 inbound leads per rep per month. 

Now, we define inbound leads as either a lead that filled out a Contact Sales form OR started a free trial of our product and met certain qualification criteria to be routed to sales.

So, go read how we generated demand and then come back to hear how we forecast revenue next.  

Forecasting Sales Headcount Based on Demand (to avoid lighting money on fire)

I mentioned we made the initial headcount mistake by dividing our annual target for new business revenue by sales rep quota to get how many reps to hire.

For example we need to add $4 million in revenue this year. Sales rep annual quota is $500K. So, $4M / $500K means we need 8 sales reps. 

Unfortunately, it just doesn’t work that way unless you have the lead flow to support it. 

Just recently in 2024, I spoke to the CEO and COO of a Series A company. They recently raised $6M in capital, doing $800K of ARR last year with a 2024 target of $2.4M (triple last year’s number). 

They have 2 AEs today and want the new Head of Sales to hire 2 more reps within 90 days of starting, so that they have 4 sales reps to hit the growth goal. They currently spend $50K/month on Google ads, which produces 70 leads total / month. Those leads convert at 10% total, so roughly 7 closed-won deals on average/month today. The plan is to continue spending that $50K on Google ads and supplement the rest with outbound sales. Average deal size is $15K. 

What do you think? Sound achievable?

Sounds risky to me. I’d much rather have a plan to send 70 leads to each rep per month, instead of relying on outbound. 

This is the Sales Forecast Template that I use now. You will see headcount is simply a function of demand (lead flow from marketing). And it factors in sales rep ramp time as well, which is often overlooked. 

Go through the same exercise for your business. Pair the Marketing Budget Template to forecast demand and the Sales Forecast Template to predict revenue. 

Then the hard part begins - when we have to get out of the spreadsheet and start to execute the plan. 

It’s time to recruit and hire the sales reps. 

How We Recruited and Hired 20 Account Executives (AEs) and 10 Sales Development Reps (SDRs)

Let me break down exactly how we did this for you.  

We use a 5 step process: 

  1. Write the Job Description: Now, you may be saying, “yeah that’s obvious.” And it is. However, you need to write the job description to align with the profile of the person you’re actually looking for. I didn’t do this initially. I just copied a generic job description for an AE. You have to do this step correctly, so that you can get the next step right. ‍
  2. Distribute the Job Description Across the Web: You want to get as many qualified candidates into the top of the funnel as you can, so you can cherry pick the best for interviews. We publish our job descriptions on the following website: our website, Linkedin, Indeed and Angelist (now WellFound). This is just to get the job out there on the internet. The best source of candidates for us always came from the next 2 steps. 
  3. Establish an Internal Candidate Referral Program: In our case, we offered $2,500 to any employee who referred a job candidate that ultimately got hired and was retained for at least 90 days. This program worked like magic. Often your best reps will have friends just like them! Looking back, I’d estimate that this program sourced 40-50% of our total hires.
  4. Get a Linkedin Recruiter License and Do Cold Outreach to Candidates: Most of the best reps out there don’t need a job. They have a job and their companies want to retain them. Linkedin provides job recruiters with an excellent suite of tools the enables you to search for your ideal candidate profile and then reach out to those candidates with a cold inMail message. They make it so easy to message candidates and invite them to apply for your open job. 
  5. Use Sales Recruiting Agencies if You are Hiring a High Volume of Candidates: There are a number of recruiting agencies that specifically specialize in sales recruiting for technology companies. We enlisted them over the years to help us fill the top of the funnel at an accelerated pace. It worked well, but looking back our best candidates still came from internal referrals and linkedin outbound. 

This process worked beautifully for quickly recruiting and hiring high-performing AEs and SDRs. 

So, we followed this process, and it generated a large pool of candidates at the top of our funnel.

Next, we have to screen them, interview them and get them to sign our offer.  

Here’s how we did that. 

The Interview Formula That Took Me From Hiring Duds to Absolute Rockstars

The very first time I had to hire a team of 6 sales reps, there was a lot of pressure on me to make all 6 hires within 2 months, so that we could start training them as quickly as possible and they could start contributing to the revenue goals. 

This backfired. 

While I made all 6 hires in time, after 4 months of onboarding and training them, I realized that: 

  • 1 was an underperformer
  • 3 were average 
  • 2 were rockstars (i.e. high producing sales reps)

We ultimately had to let go of 4 of the 6, and only kept the 2 rockstars. It was painful and a giant waste of money and time. I’ll never make that mistake again. 

Since then, the next 12 reps I hired nearly all turned out to be rockstars. At least, 90% of them. With no under-performers. 

I use a simple Sales Hiring Assessment Template.

It helps us to clearly define the criteria we are looking for in our sales candidates. Then include specific questions and exercises to qualify the candidates for the chosen attributes. Using this will absolutely blow your mind how much better your hiring becomes. 

I still use it to this day. 

Then, once we determine who we want to hire, the next step is offering them a compensation plan that gets them excited to join our team. 

Getting this right, makes or breaks the team. 

The best reps have to see a path to making a ton of money. 

The Best B2B SaaS Sales Comp Plan to Make Your Reps Wildly Productive 

Sales comp plans are OFTEN either too complicated and not aligned with the business goals. 

This was the case for us originally and the case for a number of early-stage tech companies that I’ve consulted for over the years. 

There’s a simple secret to getting your sales comp plan right to make your sales reps wildly productive.  

I use this sales compensation plan template. It walks you through a simple step by step guide on how to unlock the secret to building great comp plans. 

We ultimately decided to pay our AEs only on new business deals, uncapped their commission, and paid them double for self-sourced deals vs. inbound. 

It worked like a charm. 

They liked this comp plan because they could make real money. Some years, some reps make over $200K. It is exciting to see. 

So once we got our candidates excited about how they’ll make money, we had to onboard them and train them to full rep productivity. 

The Onboarding Playbook to Ramp Sales Reps from $0 to Closing $48K/Month in 4 Months

I’m just going to give you the Sales Rep Onboarding Playbook we use.

It includes all of the critical onboarding education that your reps will need to be successful. 

For us, we put our new hires through an intensive 2 week program before getting them on the phones and emails. 

Here’s an example of what’s inside the Onboarding Playbook: 

  • Welcome from the CEO
  • Solution Overview
  • Ideal Customer Profile & Buyer Personas
  • Industry Overview
  • Competitive Landscape
  • Sales Methodology
  • Sales Process
  • And the list goes on…

I have found there is a balance between sharing enough information to make them skillful enough to start handling leads versus too much information where you waste too much time with them not being on the phones. 

One of the companies I worked for has a 8 week onboarding program before any sales rep picks up the phone. That’s insanity to me. There’s no way you get them fully ramped within 4 months. 

I want my reps to learn by doing. 

We just route them the crappy, stale leads to start and have them do 100% outbound prospecting before sending them the Glengarry Leads (good leads). 

Then after the 2-week intensive onboarding program, we transition our reps onto our normal operating cadence, which is focused on driving continuous learning. 

The Operating Cadence That Keeps Sales Reps Working at Their Peak Performance

It turns out that success looks a lot like the consistent application of the core sales fundamentals. 

It’s not terribly sexy. It’s a lot of hard work. Just showing up every day. Putting in the time to get better and better over time. 

Our operating cadence facilitates this individual progression through a disciplined meeting schedule.  

Too many meetings and you can’t get any work done. 

Too few meetings and your pace of learning will not be fast enough. 

Here is the Meeting Cadence Template that I use to run my sales org.  

You can easily download it yourself and use it for your sales org. 

For us, it enables us to foster continuous learning, coach toward better performance and collaborate cross functionally. All of which leads to more revenue for us. 

Now it’s your turn 

You now know how our B2B SaaS company hired 30 sales reps and grew revenue by $4 million in 12 months. 

Now it’s your turn (if your business is ready for it). 

Make sure you have product market fit and a demand generation plan to feed your sales reps with leads. 

As long as those two conditions are met, it may be time to go on this exciting journey of hiring a big sales team.  

Download the Go-to-Market Playbook to access all of the systems and frameworks we used to scale our B2B SaaS company.