Forecast calls, pipeline reviews, quota attainment, unpaid commissions, internal roadblocks, lack of sales support, PIPs, end of quarter insomnia.
Sound familiar? You might be in SaaS sales.
The cloud computing boom has enabled a tremendous amount of businesses to grow astronomically at a faster pace than ever before. With the boom in SaaS tools, there has been a massive increase in the need for technical sales talent to sell those tools. And boy, did it get crowded quickly.
Over the past 10 years, I’ve seen the evolution from the last vestiges of the “old school,” mad-men type sales cultures to the inclusive, uni-corny start ups of the 2020’s. It’s been interesting to say the least- going from three $2000 steak dinners in three different cities in three days to back to back to back to back Zoom calls everyday has been jarring.
One thing hasn’t changed- SaaS sales is still broken.
The Vulture Capitalist playbook is standardized now:
- Look for small, up and coming talent with a good product (read: a product that exists) in a market segment that spends a lot of money
- Invest a shit ton of money in company
- Force company to hire salespeople (and salespeople only) to grow revenue
- Force the rest of the VC portfolio purchase the new SaaS tool (while that new company purchases the rest of the VC portfolio)
- Ask why sales isn’t selling
- Hire more sales people because sales isn’t selling
- Fire non-performing (most) sales people before they vest
- Repeat the beatings until morale improves
The common theme here? The start-up risk rests almost entirely on the sales team.
Sales is responsible for bringing in revenue that makes up at least 50% of their total compensation. No other roles in the company, aside from the founders, have that much skin in the game. If the company can’t support the revenue, the sales team feels it the most.
If a sales person is fired at an early stage company, what happens to their career? Any tenure under one year is going to get you side-eyes from recruiters, god forbid you have two or three of those on your resume. And whose fault is it?
My personal belief is that the most of the fault rests on the organization and structure of a company. The “hire sales, hire sales, hire sales” plan can only get you so far before the delivery model breaks down. There must be internal technical sales support, revenue operations, and in-house legal to support a large sales team.
On top of that, hiring more salespeople will inevitably “crowd” territories out and shrink the total addressable market for each region.
End result?
Too many sales people, not enough sales. Only the top performers are hitting OTE at most companies.
SaaS sales has evolved into a Multi Level Marketing scheme, no doubt about it. If you don’t have the top leads or accounts, you will fail. Hell, even if you smash your number, your company will likely raise your quota until you do fail.
SaaS sales has evolved into a Multi Level Marketing scheme, no doubt about it.
With some companies churning at a higher than 50% rate (according to RepVue), there has never been more interest in escaping sales and dropping the quota hanging around your neck.
But where do you start? How do you shed your golden handcuffs without losing your home or spouse in the process? Is it even possible to change careers at this point?
Fortunately, with a little bit of creativity, it’s more than possible.
I’m here to tell you how I did it and how you might be able to leverage my playbook.
If you have been working in high level sales for a significant amount of time, you’ve likely held thousands of discovery calls, sales meetings, demos, contracting discussions, and pipeline reviews.
Think about that- you’ve gained thousands of hours of experience in business strategy and operations knowledge. You’ve learned how thousands of companies operate, make money, and think at the executive level. You are a PHD level business person.
Personally, I’d take the opinion of a veteran enterprise sales person over a Harvard MBA any day of the week.
But how can you leverage it? I’ve put together a list for you.
Entrepreneurship
I’ve found one of the most common avenues to escape sales is entrepreneurship. You already know how to market and sell a product, why not sell your own?
There are, of course, roadblocks. Who will develop the product? Do you have deep knowledge of the industry? Are you solving a real problem?
Customer Success
This might seem obvious to some, but others may have a hard time “swallowing this pill.” Some might see it as a step down. Personally, I have tremendous respect for customer success. They are really the lifeblood of the business- they ensure customer retention, expansion, and that the company does their best for the client.
Yes, you’ll still have a quota (called a renewal “target”). No, it will not be as stressful. If you are lucky enough to land a Customer Success role managing 2–5 global, key accounts, you will thrive. Leverage the connections you’ve made internally to make a cross-functional move.
Better yet, go work for one of the clients that you’ve established a great relationship with.
You are the cream of the crop and Customer Success needs you.
Sales Ops
I’ve heard folks describe Sales Operations as “the place salespeople go to die.” That couldn’t be further from the truth. A true Sales Operations professional makes a tremendous impact on the trajectory of a sales organization. They increase the revenue the team brings in, makes it easy for them to sell, and help them collaborate with the wider organization.
You’ll evaluate tools, vendors, consultants, and technology to help your sales team win more deals at a higher speed.
Have you ever closed a large, complex enterprise level deal without Sales Ops? No? Didn’t think so.
On the other hand, you may have experienced the pain of being at a start-up without a true Sales Operations function. You probably understand how terrible it is. Be the solution to your own pain.
Sales Engineering
The true MVP of the sales cycle- Sales Engineering. You’ve likely worked in lock step with this team throughout your career. This is another one where you will have a “target,” but sales engineers are at such a premium in the organization, you will undoubtably be attached to numerous deals at a time. Target attainment for SE’s is a cinch compared to an AE.
A truly talented Sales Engineer will close a deal for you if given the proper tools, guidance, and time. Sales Engineers build demos, POCs, and spend time with customers onsite and remotely to achieve the all important “technical win.” If you can’t prove your product meets the requirements, you won’t win the deal.
Product Management
Don’t fall for the “you’re not technical enough” talk track when trying to pursue Product Management. The FAANGs may require a Computer Science degree, but there are many up and coming SaaS companies that need a Product Manager with a background in business.
What is the market looking for? What will sell? What won’t sell?
These are all questions that the best salespeople already know the answer for. Shoot your shot for an internal transfer, or better yet, find an up and comer in the industry you know best. If you’ve been selling Sales Compensation SaaS (my old forte), you could find any number of ICM/Commissions startups to approach.
It never hurts to get some technical chops under your belt- it’s really easy to sign up for Udemy courses or even local colleges in your area. The world is your oyster if you can do the work. Pro tip- it’s not that hard.
Cybersecurity
Cybersecurity- a little left field for a salesperson, right? Maybe not as out of bounds as you may think.
As an enterprise salesperson, you’ve likely been inundated with Security reviews, Privacy Impact Assessments, Data Processing Addendums, and RFPs. You’ve also probably had a hand in quarterbacking them- which question goes where, how to answer accurately and still get the sale, etc.
There is an entire undiscovered need for cybersecurity sales enablement. It is technical, presales type role that doesn’t necessarily demo to prospects, but does “ride along” for technical product conversations.
Overall, you’ll be working with the sales team to unlock deals that are stuck in the security review process. You’ll work your “sales” magic on the Information Security blockers at the prospect and make them comfortable with the fact that your company will now be holding their sensitive data. You’ll become very popular in your organization because your are the easy to work with, knowledgeable, badass Cybersecurity consultant.
Conclusion
You’re tired, burnt-out, and anxious. You NEED a new job, but can’t imagine a world outside of sales.
I’m here to tell you that the grass IS greener on the other side. Drop your quota, drop your stress, and live your life.
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