From Field Sales to SaaS Sales: Solving the Sales Talent Shortage

Ask any SaaS sales leader today their biggest concern (besides hitting their number, of course) and you’ll hear the same thing: recruiting.

There is a serious shortage of high tech sales talent out there today, and it’s not getting any easier. Far too many SaaS companies are fighting over the same small pool of skilled sales reps, creating a bidding war for the top talent.

However, many SaaS sales leaders are ignoring a resource right at their fingertips. Instead of looking for the same recruit over and over again, there’s an opportunity to find and train talented sales reps that could thrive in SaaS — with the right guidance and training. Instead of focusing solely on reps who have done it before, you can find outside sales reps who can quickly and easily adapt their skills to high tech inside sales.

High Tech Sales Roles Are Harder to Fill

Days on Average to Fill a Tech Sales Job
Days on Average to Fill All Other Jobs

The Mythical Rock Star Rep

I’m building the West Coast Sales Team at InsightSquared right now, and experiencing this shortage myself. We opened a satellite in San Francisco, and I have to fill the seats. Our CEO and VP of Sales tell me to be patient and recruit the right rep with the right skills and the right background. They want me to find a rainmaker — the rep who says, “Just give me a phone and a list.” I get it — I was that guy. But hiring that rockstar rep is easier said than done.

Those reps are almost never on the job market, and if they are, they’re snatched up immediately. If a company has killer sales reps, they’re offering them whatever it takes to get them to stay. Almost everyone in SaaS is trying to hire the same few sales reps for their team, and you may not be able to win out over the competition. You simply can’t rely on recruiting a rockstar SaaS sales rep to carry your entire sales team.

Think Outside of SaaS

Instead of fighting for the same 5 SaaS sales reps as everyone else, broaden your search and think outside the high tech box — in fact, think outside sales. You may be skeptical at first, but it is possible for an outside sales rep to successfully switch to inside, high tech SaaS sales. You simply have to identify natural sales talent where you see it, recruit them, and then train them thoroughly in the skills they need to switch from outside to inside.

How do I know this works? I switched from outside to inside sales myself. I spent 7 years as an old-school field rep. I was a road warrior and a steak dinner guy, selling laundry contracts to hospitals and factories throughout New England. I made President’s Club 5 years in a row, and then opened up 2 new offices for the company.

Why did I change from selling sheets to selling SaaS? Funny story — there are no margins in laundry. So, the super sexy sales gigs these days are tech or med device. And I’m probably more comfortable with a laptop than I am with a scalpel. So off I went.

The weird thing is that most of the people I meet in the tech community think it’s crazy to not come from tech. It sounds unfamiliar to them that I don’t point to some legacy hardware gig as my background. I think this represents a huge mistake in our industry’s recruiting and hiring strategy. Your future stars are actually at Enterprise, ADP, and Cintas right now. Here are my personal learnings to help guide your outside to inside sales program, and prepare these reps to sell SaaS products over the phone.

Adapting to Inside Sales

When I came to InsightSquared, I had to change a lot about how I sold. I was used to in-person meetings, where I knew the name and title of everyone in the room. I actually shook hands with every prospect to close a deal. They were large deals, and I only needed a few to hit goal.

When I came inside, I quickly realized that I had to adopt a new approach. Here are my 5 biggest takeaways from transitioning between outside to inside sales:

1. Keep It Personal: Instead of meeting people in person, we do most of our selling over the phone. The efficiency gained through an inside model means you can touch so many more people. However, phone calls are impersonal. I’m better when I can read emotions and see reactions. Just because you’re selling remote doesn’t mean you should submit and let the situation rob you of your humanity. Every laptop has a webcam now, so just use it. Turn yours on and your prospect will too. Or ask them too. I like awkward. It humanizes you. Get face to face even when you’re not really face to face.

2. Stop Everything: The other challenge with inside sales is that sometimes, you’re ambushed by a person who you didn’t realize was on the call. Suddenly, a mystery guest is throwing flaming balls of hate your way and never even introduced themselves or made their intentions known. Stop. Every. Thing. Politely address the fact that you’re a human being having a conversation and ask them their name. Find out what they do there. Find out why they’re asking what they’re asking. Then, acknowledge their question and deliver an honest answer. Command the room and don’t let them push you out of your square. It’s cringeworthy the first few times you do this, but it’s worth it. By maintaining your position as the subject matter expert, and by demanding a conversation on equal footing, you’re establishing a better engagement from there on out.

3. Build Your Social Brand: I also realized quickly that your online brand matters a lot for inside sales. Before I started working at InsightSquared, I barely had a LinkedIn profile and didn’t use Twitter at all. It just didn’t matter for laundry. But with inside sales, it’s vital to invest in social selling. Prospects need to feel like you’re accessible, trustworthy, and knowledgeable in the field. Make sure you create a great LinkedIn profile, that positions you as a credible advisor. LinkedIn is not your resume; it’s your professional social media page. Share relevant content. Join the right groups. Have conversations and engage with people.

4. Transactional Sales: When I was working in outside sales, I was able to close just a few deals and hit my goal. In SaaS, the deals can be smaller and more transactional in nature. It meant that I had to shift my goals and work more deals at the same time. This required better time management and focus on my part. I suddenly cared about MQL:opp ratio by lead source and by campaign. I cared about conversion rates for different contact personas. My focus is scale and efficiency. You find a way to consistently take the smart behavior and model it across your team. Find the mistakes and eliminate them.

5. Trust the Data: When I worked in outside sales, I just kept track of my deals on my own and told my boss about them. He didn’t care how I engaged with prospects as long as I closed deals. But for inside sales, CRM usage is incredibly important. You have to log every call, take notes on every interaction, and look for patterns in the data. Sales data is a powerful tool for both managers and reps, and inside sales needs these insights.

These are all lessons that I learned quickly on the job when I switch to inside sales. I was able to become the top sales rep at InsightSquared, and other reps can do the same.


Next time you’re struggling to fill a vacant spot on your sales team, don’t be afraid to bring in someone who doesn’t have a tech background. With the right skill set and targeted sales coaching, you’ll be building the next class of rockstar sales reps to kill it on your team.  If you’re building a team, I hope this is helpful. If you’re looking to join our SF team, come and find me. 🙂