What 20 years in SaaS sales gave me

READ TIME: 5 MINUTES

Two calls this week. Same question, different angles.

One had built a successful career in medical devices. He's thinking about breaking into SaaS sales and wanted to know if it's worth the jump.

The other had spent years in SaaS. Good runs at a few companies, 4 to 5 year stints, exceeding quota, top rep. But across that career he'd also had the short ones. A layoff. A company with no product market fit. Enough of them stacked up that he was asking: should I even stay in tech sales?

Neither of them said it this way, but here's what they were both circling:

I don't know what my next step should be. And I don't want to get it wrong.

I can't answer that for you. But I can tell you what my 15 years in SaaS sales actually gave me, and why I'd do it all over again.

I got into sales for one reason. The money.

I was a college grad trying to move to DC, and I learned fast that working at a nonprofit wasn't going to pay my bills.

At the time I thought of sales as sleazy. Even though my dad had built a successful career as a seller in the hardware space.

Looking back on my SaaS sales career, I'm thankful for it. Not just for the financial stability it built. For the skills I walked away with.

3 things sales taught me that I still use every day

1. Communication

How to ask open ended questions. How to listen.

That skill has supported my ability to run an effective meeting, coach, hire great people, sell myself in interviews, and present in front of a room.

2. Process

How to confirm a meeting. How to follow up. How to drive a decision or a project forward.

I used it in sales. I used it in leadership roles. I used it in my job search. I use it now running my own business.

3. Data

Sales math. Understanding why KPIs matter and how to break apart data to find the root of a problem, then focus there.

That math helped me exceed my personal sales quota. It made me stronger in leadership roles. It helped me launch a successful metrics driven business.

You'd learn those 3 skills in any sales role.

What sets SaaS apart from medical device or physical goods is the margins. Stronger margins mean they can pay more. That's the piece people underestimate, because what you do with that money is what buys you options later.

How I actually used the money

Early in my career I set my standard of living around my base salary plus 50% of my commission.

Anything above that went to paying down debt, investing, and one splurge.

I backed into my commission plan so I understood exactly what I needed to do to hit certain numbers. Then I set goals against it. This drove my performance. I was personally tied and invested in my numbers.

If I got a $10,000 commission check, $5,000 went to vacation, $2,500 to debt, $2,500 to investments. I always maxed out my 401K.

That strategy gave me the financial freedom to face 2 layoffs, take a 1 month trip to Australia before starting a new role, purchase a home, and start my own business.

So why did I leave?

If I learned that much and benefited that much, it's a fair question.

I'd been debating it for years. My plan was to launch this business in my 50s and semi-retire. In the last 3 years I started to ask: how do I work less, spend more time with my family, coach more, and remove the stress of sales leadership?

For me it came down to time flexibility, coaching, and building my own business instead of someone else's. The money was no longer my primary driver.

If my north star looked different, I'd still be in tech sales.

And if I were earlier in my career, I'd stay. I'd do it all over again from the beginning.

Which brings me back to those 2 calls.

If you're deciding whether to stay in SaaS or break into it, I'm not going to tell you yes or no.

What I'd do is work with you to get clear on what you actually want, weigh the real pros and cons, and support you to make the best decision for you.

That's the work.

Hit reply and tell me: why are you in SaaS sales? I read every response.

To clarity and confidence in your career path,

Amanda

See you next Sunday.

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