How to Land a SaaS Sales Job in 60 days Part III

This is the last update on previous posts I’ve written about “How to land a Job in SaaS part I and part II are covered here and here respectively.

About midway through the process of interviewing, despite my confidence, I ended up running into a couple of walls that led me to shift my perspective and strategy on landing a new role. Specifically, I had an interview with a company in the SaaS and R&D space where I had been turned down by the hiring manager because I lacked a few things:

• Domain expertise

• Deal exposure was not big enough

• Ramp up time to learn both the sale and learn the industry

This frustrated me to no end. Especially since I was PUMPED about this role. The recruiter (internal) had gone to bat for me and set up time for the hiring manager - he believed that I was a GREAT fit for the role given my experience.

All this to say the hiring manager did not feel the same. To her credit, she did provide feedback upfront which provided the opportunity for me to overcome those concerns. Nevertheless, it was a show stopper.

This particular interview hit me pretty hard from a confidence perspective. Additionally, my pipeline of roles had and was drying up fast. I just wrapped up teh final interview with another company in the space and knew that I did not do a great job with that process so was not expecting an offer.

Needless to say, when I initially had embarked on this journey I thought that the process was going to be MUCH easier. I had a few good runs in multiple roles, and a decent chunk of change of enterprise sales experience. And now … nothing. I was in a pretty rough place mentally, completely demoralized. It’s probably safe to say that if you’ve gone through the interview process recently, or had been a part of lay offs, you may have felt, or feel the same as well. It’s certainly frustrating as I had multiple opportunities where I had gone pretty far down the funnel and ended up coming empty handed!

Aside from revamping my outreach strategy, I had to sit and think about these experiences in a different way. Which led me to ask some philosophical questions that helped guide me through the process more efficiently and in my opinion, opened me up to more opportunities.

In time of stress or uncertainty, I try my very best to try to separate myself from the emotions that I’m going through and focus on two variables:

• What can I control?

  • Action Items

• Simplify

  • Key insights

    • What do you want in your ideal job?

  • Refined New role requirements

• Am I asking the right questions about my approach?

  • Leverage

    • Save Money

    • Leveraging Domain Expertise

    • Managing Career Proactively vs Reactively

  • What could I have done differently?

(I’ll unpack this more below)

What can I control?

The main thing that I could control was where my efforts were best being placed. It probably comes as no surprise that though I can fire off applications … this was probably a waste of finite energy that I could be using towards somewhere else that would yield more productive results.

Asking recruiters for help. Here was a situation where I can reach out to a couple that I had trusted but the reality is that I have that set up as an inbound channel, not more. I was getting some intros via my network (but only a select few). Where was this getting me?

Yes it made some progress but what happened if I increased volume? What happened if instead of applying I would use that time to see who in my network is connected to companies I was interested in and can get me referrals? What happens if I asked CUSTOMERS to point me in the right direction or even make intros for me?

• Action Item: Channel mental bandwidth to networking with AE’s in market for roles, cold email hiring managers, and asking customers for help.

The other big thing that I thought about was LEVERAGE. I wanted to be in a position where I had leverage, and that can come in many forms. The most obvious is multiple companies vying for me to work for them. The other is having domain expertise in a certain area. The other was also shifting my narrative from “expert” to “ expertise”. And ultimately being in a position where you have cash in the bank so that TIME is on your side.

• Action Item: review finances to see your timeline to landing a job in a worst case scenario set up timelines to have multiple offers for you to decide from, look for a job when you have a job

Simplify

I was getting to the final rounds of interviews because I was dead set on getting a role in the infrastructure space. To me, this was a baseline in terms of where I can be in opportunities to close big deals and make a ton in commission.

• But did this really matter?

I had gone through a cycle of interviews, mostly final rounds. There was three conversations that I had with both hiring managers/teams along with one person in my network that starting turning on a few light bulbs.

• Some key insights:

  • From two hiring managers - I lacked certain qualifications that made them hesitate about me “hitting the ground running”. Ie some companies I had gotten into because of my pharma experience and had a tech/science blend to them. But the further I got into the process, the deal stopper was not knowing the “science” language of these key personas. Or other times was not having exposure to “big enough deals”. Interesting …

  • The other show stopper was that despite closing massive net new logos - I didn’t have exposure to “big enough:” deals. This was somewhat surprising to me as I imagine that the exercises I was going through to break into net new logos that I had in my prior role, would translate seamlessly into an enterprise cycle with a high price tag. Now, maybe I didn’t position myself well enough, or maybe that is what the actual case was from hiring managers.

The hiring managers feedback and concerns (which I actually appreciated the fact that they were so candid with me because it gave me an opportunity to respond but also understand my place in the market and where I could add leverage. And leverage is the most important take away I had from all this.

I ended up reaching out to other more veteran sales people, using this tactic as an approach to not only get insight on how they managed a rough bump in their career, if at all, but also to get into companies that I had targeted.

This conversation really put me on my hand and prompted refining my target search. And ironically, it was the simplest question of them all that I just didn’t really flesh out when I embarked on this journey.

• From one senior sales person in my network: “What do you want in your ideal job?”

I should have been easily able to answer this question but I was stumped. It blew my mind that I stumbled on it and had to think it through. You might be reading this thinking well no shit dude.

But the simplicity of the question was something that I struggled with. And if there’s anything that I’ve learned from sales, is that the simpler the language and concepts, the better you can communicate and get to where you want to go. This works in sales, life, and ultimately, networking for jobs.

This led me down narrowing segments while also being more buttoned up on these concerns that I knew would surface and it really forced me to take a practical approach to my job search.  Ultimately, I knew that there were segments that I didn’t want to sell into and segments that though I was dead set on getting into (ie dev ops). But that didn’t necessarily mean that I couldn’t be getting the characteristics of the job that led me down hunting for technical sales.

My new role requirements:

• Data (not necessarily even dev/infra/cloud, but in some way connected to data)

• Large deals and large enterprises

• Recession proof - is the product tied to industries that will succeed despite down markets?

• Mission critical - is this a product that is necessary for a certain business unit?

• Executive stakeholders - is the sales cycle important enough to get on the radar of a VP or C level stakeholder?

• Stability - I don’t want shiny and sexy, I want boring and necessary

• Remote or Hybrid … preferably remote

It’s worth noting that these guidelines show that there a lot of ways to connect the dots on getting what you want, in any given an industry, territory, etc. I’m sure that there are nuances in each. Happy to dive more into that if people have more questions in a separate post. The important thing is how does it tie into a narrative that helps me elevate my sales career and place me in a position to get to where I want to go.

With this north star, I was able to start concentrating on sectors that I had some familiarity with but it was an aside from the initial tiering that I had put together. If a company had checked those boxes above, it was a go. If it was big, great. If it was a startup, I had to do some further vetting (also happy to share how I vet a startup).

Because of this, I focused on my network to get me to those people, along with cold emails. The initial design being, what were the things that the company was seeing and how can I come prepared to interviews being able to sell myself on this. And also, was this a good company or a shit show? (I’ve explained this tactic in part II).

These were all things that I had pieced together to set up a narrative. And a narrative and story, which given we’re all sellers here, come as no surprise. People respond to narratives and stories. When I think back to objections from coming down in the hiring process, I was focused on a quick synopsis, highlights of what I had achieved, but not crafting a story on the why I would be a good fit, despite concerns or challenges.

Of course, your story might not always land, that’s okay. But in some conversations it will stick. And you will tip the scales in your favor when it comes offer time. And there will obviously be conversations with companies that will be natural evolutions, ie if you’ve sold to cloud security platforms to developers in the mid market role, were promoted to enterprise, you can easily shift gears to a company which is in a similar space. This happened to me but it wasn’t a direct shift into the same audience.

Leverage

The other key insight that had dawned on me, which is also probably a “no shit” moment as well is the following:

• Save your money

• Domain Expertise

• Managing Your Career When Employed (proactive vs reactive)

I’ve broken each down in the bullets below to unpack that more.

• Save Your Money

I can’t tell you how many tweets or reddit posts I’ve come across where sellers are in the undesirable position of having to find a job fast to get their next paycheck. This isn’t a knock on anyone who’s in this situation, I’ve been there before. It sucks. And this will put pressure on you to find your next role. All that said, I’ve spoken with one rep who landed a new job WITHIN 16 days with pure grit and hustle. His quote was fantastic:

“I don’t have time to cry on LinkedIn, I have kids who need insurance and a famliy to provide for so once I got wind of layoffs I cold called hiring managers as soon as I saw the posts come up”.

If you’re in a position where you don’t have a timeline because you’re pressed on timelines to get income, I feel for you. But certainly use it as a lesson to save your money to ensure you’re not in that position again!

• Domain expertise

I heard a quote from one seller, which I think came from Jim Keenan on LI (and I could be butchering this) but “Stop selling that you’re an expert and sell your expertise”.

If I take a look at my profile, I realize that here are som key areas that I have expertise in:

• Breaking into net new logos

• Martech

• SaaS/tech sales

• Pharmaceutical industry

• Building out teams and revenue for startups/young orgs

The last bullet point I leaned on hard because it showed that I knew what it took to take a sales org with little to no exposure to the market, to one that was a at least predictable.

Blending this or all these points on interviews framed the conversation away from pitfalls and objections towards the reality that no one has done it before and THAT’S what I’m good at. Becoming a domain expert, while certainly a plus, is all in all, learnable.

The real value is that I’ve been working at startups my whole career. I know how to BUILD. How to identify what works and what doesn’t - and quickly. How to pivot. How to come up with a strategy based on what I see already that is working or is viable. How to scale or win in environments where I don’t have all the resources negated whether or not I was an expert in a certain domain.

• Managing Your Career Proactively vs Reactively

As the saying goes, it’s much easier to find a job when you HAVE a job. Now, some things are unpredictable but I find often that many sales reps are comfortable and don’t want to be proactive.

If I had done that, or have been having convos, maybe I could have landed a job much quicker? Who knows, the reality is that I fell into this camp. Won’t happen again.

I’ll be doing the stuff I’m doing here - though not as aggressively, to ensure I’m not in a situation where I have to be looking for a couple of months. Nothing is guaranteed, but I’d rather have some groundwork laid out.

What Could I Have Done Differently to Make the Process More Efficient?

Now that I’ve landed a new role, the question that immediately came to mind was … what could I have done better? My initial goal of landing a job by the beginning/mid March extended well into April.

What’s interesting about networking is that you end up running into a lot of people and a lot of different ideas. Talking to other people in the same situation is therapy in and of itself - you’re not alone. Highly recommend doing the same and just helping out where you can. It also gives you new ideas that you can implement into your strategy. I’ve gotten this from people who are more senior than me and more JUNIOR than me.

Tools and tactics I would have used that might have made this go faster or more efficiently:

• apollo.io or Hubspot. Some type of CRM to track this stuff better. I was diligent on an excel shit but damn that sucked. I could have been more organized, but don’t think that was the ultimate showstopper.

• Call hiring managers - DUH I picekd that up from the preson who found a job in 16 days. I was in the later stages with most folks and had networked my ass off to all the companies I wanted to get in front of … but damn this was a dummy/rookie mistake.

  • If I had done this on the get go- maybe I would have been in front of hiring managers and closed on a new role in half the time. I don’t know, but

And if you’re junior in your career and reading this. Don’t be afraid to pick up the phone. Sales mangers love that shit. What sales manager wouldn’t? And if one call goes bad, identify what didn’t go well, rinse, repeat and continue. If you’re nervous, target tier 2 or tier 3 companies to shake off the cobwebs and get you into the flow of doing stuff.

Conclusion

• Serendipity is a thing …

Open yourself up to opps cause you never know whats out there. I ended up taking a new role that checked the boxes for career progression, thoroughly vetted via network (for leadership, quota attainment, product, and mission criticality and segment).

Where I thought I would end up was not where I did. But nonetheless it’s an opportunity. And it plats well into my narrative and overall, I’m HAPPY where I landed.

• Nothing is permanent

I imagined that I had to have the perfect role with all the perfc things - I might have been being too picky. Nothing is perfect and with that nothing is permanent. Careers, like life, are fluid. Show progression, learn, make money, and move onward and upward.

If you have more follow up questions, please hit me up! You can find me on askobylarz@gmail.com or @askobylarz on Twitter.