How To Transition Into SaaS Sales

by Jeff
(Providence, RI, USA)

Hi, I'm trying to figure out how to transition into SaaS sales. I read you used to be a personal trainer and made the switch from fitness to SaaS. I've applied to hundreds of job postings, gotten a bunch of first interviews with a few companies, and a few second interviews. But, at some point they usually mention my lack of SaaS experience or they end up hiring someone with more experience from what I can tell (they don't always let you know why you're getting denied). What did you do to make the switch?

Thanks For Your Question, Jeff!

I appreciate your visit and question. It sounds like you're encountering some obstacles in moving into SaaS. I've been in similar boat before, especially where you mention sending out 100s of applications. I lost count of how many I'd sent and 1st interviews I'd been on. There is a light at the end of the tunnel, and I'm happy to share a few ideas that may help you on your journey.

How To Transition Into SaaS Sales

Below I've outlined several of the steps I've taken, not just in transitioning into SaaS, but in moving from one role to another no matter the industry. I've included links to a few resources that may be worth your while - they were for me. Some of these may be affiliate links for which I receive a small commission should you click through and purchase, though this will be at no additional cost to you. I'm picky about what I recommend, so hopefully they'll be of use. For more on this, read our Affiliate Disclosure Policy.

Update Your Resume

The first thing I'd do is update your resume. You didn't mention if you're coming from the fitness industry, though I believe this step is key no matter what industry you're coming from. When I switched from fitness, there seemed to be time in first interviews that was dedicated to explaining that the fitness industry isn't just about sneakers and sweatpants; that there are KPIs, sales quotas, profit and loss, and cold outreach among other things. From my viewpoint, the fitness professionals I know and have worked with may be overqualified for entry-level SaaS roles as they've usually been tasked with more than I've seen SDRs, ISRs, and AEs to be responsible for.

Back to the resume. Where you're able, include detail as to your previous performance related to KPIs, quotas, and other achievements. If the terminology for these areas isn't an exact match, given the differences in industries, be prepared to describe each in the phrasing that your interviewer will best understand.

As a general recommendation, update your resume monthly, even if you aren't actively applying for a new role. This way, when you're pressed to apply, you won't be scrambling for details.

Update LinkedIn

LinkedIn is the primary site for career connection and opportunity. For years, people treated it as an online business card, or just a copy of their resume, and not much more. Recent years, and technology updates on the platform, have seen people making use of daily posting, newsletters, continuing education, and more. I'd advise making use of these, and not logging into LinkedIn only when you're on the job hunt. If we've not connected there yet, here's my LinkedIn profile.

Networking On LinkedIn

It's unusual that I don't accept connection requests on LinkedIn (though with its growing popularity, I've noticed more profiles that do appear to be "spammy"). I'd advise against being overly protective in denying connection requests. If you only wanted to connect with people you already know, that's what Facebook (or is it Meta?) is for. LinkedIn is similar to traveling to industry conferences. It's an excellent place for meeting new people who may have professional interests that are similar to yours. And, where you're intent on transitioning to SaaS, you may not yet have a strong network in this area. In considering my own network, I enjoy the variety of entrepreneurs, educators, fitness professionals, sales people, and more whose posts I'm able to engage with each day.

A general recommendation here is to seek those with whom you'd like to connect. They may be HR personnel or hiring managers at companies you're interested in working with. Or, they may be people in the roles you're most apt to enter, whether SDR, BDR, AE, etc. Connecting and beginning conversations can open doors to a wealth of information that can support your journey.

Writing On LinkedIn

I mentioned not leaving LinkedIn to be an unused resource, yet to be something you use more often than not. Part of this may be accomplished in building a habit of writing each day. This might be in the form of writing your own posts, reflecting on information that you know well, and that can inform or inspire others. Or, it might be in the form of writing comments (something of more value than just "I agree.") on the posts of others. Above, I talked about certain resources that I'd recommend. And, Justin Welsh's "The Operating System" is one of them. It is the single best course I've taken in the last several years, outlining a precise system for improving your LinkedIn activity and engagement.

Writing doesn't come easily for everyone. Hitting "Post" can be an obstacle in itself. What I usually mention to coaching clients is this:
  • More people are afraid of hitting publish than not.

  • You've gained information and expertise that is unique, based on your previous experiences.

  • You're further along in your career journey than someone else might be, and your knowledge is going to be of value to them.

  • Pretending you're writing to just one person can make the task seem far less daunting.

  • You'll learn more by taking imperfect action now, than you will in waiting to start at all.

The Non-Traditional Route

I mentioned getting numerous connection and meeting request daily. I'd say it's less that I have any sort of major LinkedIn status, and it's more the nature of my consistency of activity on the platform. Whether you're being reached out to, or if you're doing the reaching out, it's important to find a way to stand out from the crowd. This is another good reason to move away from some of the talk tracks that have gained popularity, and just work on being you. One great way to accomplish both of these things is through the use of video as part of your introductory messaging. I'm a huge fan of Vidyard and have used it in outbound sales roles, in my coaching and consulting practice, and in providing customer service. It's a great way to start conversations, earn initial meetings, and to follow up as you progress through stages of the sales cycle.

Practice Interviewing

So, now you've done all this work to get your foot in the door, and hopefully get a few more interviews. But, we still want you to be comfortable, well-polished, and well-prepared to make great impressions. Most of the interviews I've had since 2020 have been conducted virtually. And, just as you want to keep your LinkedIn profile from gathering dust, the same can be said about your interviewing skills. It's not a bad idea to have a schedule of mock interviews. Send a friend questions you'd like them to ask you, and have them come up with a few interview questions of their own. Schedule a time to meet in video conference, and give yourself the opportunity to hear yourself answering the types of questions you're likely to hear. Be sure to dress the part, too. When it comes time to perform on the actual stage, you'll have that much more confidence because of your dedication to preparation.

Quality Over Quantity

You mentioned having applied to hundreds of jobs. For a while, I'd done the same. While it might seem like the path to opportunity, your interests might be better served in prioritizing the quality approach. Prune your list of companies you'd like to work for. Review their websites. Understand the mission, vision, and values. Connect with key stakeholders. Discover their paths and interests. Write a cover letter, specific to that organization, and connect the dots on how you can be of help. This takes time. Though, your quality investment of time should allow for greater impact and opportunity than the spray and pray technique. When you do get your desired role, you may find this practice to be of benefit in engaging with prospects at key accounts, as well.

Attending Webinars

Most organizations host some sort of online webinar to engage with their prospective clients. Attending these, as a prospective employee, is an underutilized tool for beginning conversations, learning company-specific phrasing about products or services, and meeting team members. When you mention that you've attended webinars with specific hosts, you'll stand out among the applicants for the roles you're interested in.

Your Health

Being on the job hunt is taxing. The urgency, uncertainty, and rejection can wear on you. Don't spend every waking hour applying. Schedule your days to include the professional stuff: your research of companies, your practice interviews, and your LinkedIn writing and networking. And, schedule your personal things, as well. Schedule time to read. Schedule time to workout. Schedule time with family and friends. Schedule time to detach from technology. Finding harmony is a superpower. You'll be happier for it.

Great Luck!

Thanks again for your question and for being a valued visitor. Best of luck in your journey. As you have more questions, please do reach out. We'll be cheering you on!

In health,

David Bohmiller, MBA (he/him/his)
Founder, CEO and Consulting Executive
Inevitabl LLC

Comments for How To Transition Into SaaS Sales

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One Other Thing I'll Mention
by: David Bohmiller (Inevitabl)

Jeff, I'd be doing this post a disservice if I didn't also mention the importance of staying in touch with former colleagues. I'd be remiss if I didn't thank Sean Lee for his guidance and support, as he'd made the switch from fitness to educational technology / SaaS earlier than I had!

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