How to Land a Job in SaaS Sales in 60 Days Part II

Resource for folks who are looking to break into tech or recently laid off. If you haven't already, check out part I as this post is an update on progress, tactics, and strategy.

This is an update to a post I wrote about how to land a SaaS Job in 60 days. I’m excited to say that I was able to get two offers, and accepted one. Total time to get a verbal offer was 10 weeks and 6 days. So definitely a fail on the 60 days part, ouch! But nevertheless, landed a new role. I provided some numbers in my initial post and here are the updated numbers.

Total

• 105 total touches (this includes 45 applications that I had initially posted, I stopped doing this - more on that below)

• 26 first round interviews total

• 12 later stage interviews

• 2 offers

You’ll notice I said “touches” since I stopped stopped applying. I became much more focused after my last post on finding quality. Some might disagree with this but it’s the strategy I took. If you look at updated numbers from that perspective, it’s far more efficient:

Updated after last post

• 60 total touches

• 11 first round interviews

• 8 later stage interviews

• 2 offers

Total investment into resources

• resymatch.io $39 x 3 months (no affliate link)

• Job search course from Resymatch: $200 (one time purchase)

• Email playbook: $19

• Coursera: 2 months X $49

In total, starting from 1/23 I ended up closing the gap from no job to verbal offers and signed within 10 weeks and 6 days (1st verbal) and 11 weeks and 1 day (2nd verbal). Final offers signed on 4/6 totaling 12 weeks.

If I further breakdown the timelines, I actually was able to close on jobs with my refined approach after 2/28 - total time being 4 weeks.

You’ll notice that my conversions rates throughout the funnel were much higher, ie once I landed a first round interview I’d land more and continue down the funnel. I ended up even turning down jobs midway through the process of some interviews and ultimately pass on offer.

I was off by about 4 weeks in being able to land a job in 60 days. Ouch. But nevertheless, it’s a competitive market so happy that I landed something. It also felt nice that I finished the process with options instead of having to take only on offer.

My strategy completely shifted after an interview on 2/28 and this made me realize a lot of things. I’m going to write a follow up post to this to walk through the stories that made me come to these realizations and provides more insight into how I tailored my search following 2/28. All that said, the first actionable items which I think that anyone can apply in any market, no matter how competitive it is:

• Network and get in touch with PEOPLE like your life depends on it

  • Stop caring about what people think and take action

  • Referrals and Customer intros provide insight into good companies

    • If you are cold calling, or cold emailing then modify after you get a green light from your hiring manager.

    • If you don’t have a network, then cold email or cold call, THEN write your resume.

• Your resume and LinkedIn are marketing tools, use them that way

  • The first step is getting in touch with your network and THEN modifying your resume.

• YOU are the the product, and during interviews you’re selling the product, aka YOU. Listen to market feedback and modify your pitches accordingly. Don’t take anything personally, it’s simply business.

Network like your life depends on it

The reason that I stopped applying for jobs was that I was taking too much time using a software called resymatch.io to modify my resumes for each application. This isn’t a knock on the service, I highly recommend it. I’ve used it once I got an intro via an AE or customer to a hiring manager. It’s only $39/mo and quite frankly the ROI is there. This was just my own mistake of “feeling” like I was getting myself out there when in fact it was eating up hours on jobs that I identified that I wanted.

I started thinking, what’s the best way to get in front of hiring managers? Obviously, word of mouth. Just like getting customer referrals. This meant that I had to identify people in my network that were both good performers and good people (this part is key).

I also wrote down a list of customers that I had worked with both in my previous role where the sales team was downsized, and my prior role where I had a nice 6 year run. The customer list was orchestrated with folks that I had good rapport with and in my LI network.

If you don’t have a lot of customers, maybe because you’re just trying to break into SaaS or feel like you didn’t have great rapport - I’d suggest reaching out anyway. People like to help, and I figure customers will know whether or not a product is a good offering, and will be connected to hiring managers. This is the golden egg, IMO. Having a customer reach out to a VP of Sales I think speaks volumes, even over an AE on the team.

• Stop caring what people think and take action.

End of the day, I stopped giving a shit about what people thought (take this with context and candor), and just started taking action. Seriously, if you’re hesitating on something - just do it. Nothing will break.

Also, no one in this world is going to get something for you. You have to get it for yourself. This isn’t to say that people won’t help. But the feeling of having your back up against the wall and having NOTHING to lose is a swift, yet refreshing, kick in the ass.

• Referrals and Customer Intros equip you with key insight into companies

When you are doing research into companies, it’s key that you identify people who are second connections to people you know, or are on the sales team you’re looking to get hired for.

If they’re second connections on LI and you know a person well - ask for an intro. If you don’t know them well but you love a company then COLD email. I’ve taken the approach of cold emailing/cold LI messaging both hiring managers along with AE’s on the team. Take the same approach with hiring managers.

For hiring managers

• Second connection or direct intros

If I was a 2nd connection, I’d ask for an intro from that person in my network. This allowed me to get a sense of the hiring manger from my second connection (ie are they a good leader/good person to work for?). Undoubtedly, getting an intro from a 2nd connection, considering they’ve worked together before and recommend them, or work for them currently, will guarantee an interview. If you’re qualified, it will also undoubtedly fast track the interview process and significantly increase your chances of landing a role.

It goes without saying, this is the lowest of low hanging fruits and effortless aside from a quick couple of minutes of research.

• Not a second connection, reaching out cold

In this scenario, craft an email to a hiring manager, or exec (if it’s at a small startup) with reasons why you’d be a good candidate along with why you’re interested and a strong CTA, ie time to meet.

It’s important to be short and to the point. VP’s of sales, like most VP’s, are all busy as hell. And their inboxes are probably similar to that of other key execs that have vendors knocking on their door. You can do this with email or LI messaging, followed by a connect. Happy to share tactics if people request.

Cold calling

Same as above. You can use apollo.io which is free (at least least I heard) for candidates looking for jobs and find names/numbers. I’ve used whitepages before in my other jobs if I needed to get info for key stakeholders whose numbers were not in my stack (zoominfo). Not koshur, but sometimes you have to bend the rules.

If you’re scared of doing this keep the mind frame that you’re doing them a favor. I’m sure they’d appreciate a cold call from a proactive, and potentially qualified candidate to fill a role. And as mentioned above, this action would certainly fast track the process.

Ironically, I did not cold call hiring managers. This was a … silly mistake on my part. I ended up talking with someone (AE intro to hiring manager) who closed a job in 16 DAYS by cold calling and using apollo.io. There’s more context to this and I’ll break this down in a future post but shame on me for not doing this. By the time I did connect I already had enough traction and work with all the processes I was engaged in, and close to offers, so ultimately never did.

The only hesitancy I have with directly reaching out to hiring manager, and people may disagree with me but … the hiring manager is selling you on the role as well ,if you’re qualified. I find that getting intros equips you with key insight on companies as well as inside baseball on how the team is doing vs getting that lens from a hiring manager who is motivated to fill a role. Though the process may take longer, it’s more of a qualifying tactic for me, and though this interviewing process is very similar to a sales process when it comes to interviewing - the key difference is that I’m going to be in that for years and I have to vet out how that impacts MY career.

This leads me to other approaches I took, and quite frankly preferred, which was reaching out to other AE’s.

For AE’s

I personally preferred going the route of reaching out to AE. It was slower but you are equipped with a lot more info, by design, before you get in front of the hiring manager. Also, this is a qualification tactic. Remember that the overall goal here is to land a job you like, once that aligns with your career and interests, your targets, and one where you can hang your hat for a couple of years.

This allows you to sell yourself better and talk to points that are top of mind for higher ups. It also allows you to qualify a hiring manager and opportunity better. If the product sucks, or the hiring manager isn’t that great, why bother?

I also like the idea that I’m speaking with a potential peer, and with that, their motivation to take the time to speak with you is a referral fee. Hiring managers will be candid but they are selling you on a role as I had mentioned above, and their motivation is exactly that, so long as you are qualified - fill the role.

The AE’s perspective is different. I look at it through the lens of myself. If the candidate does well and I get a referral fee - awesome. Happy to help take 30 - 45 minutes to help out and maybe pad my pockets with extra cash later down the line. I would 200% take a convo with someone and if they seem smart, were pro active and reached out to me, I’d put their name in the hat. I’d also provide this context to HR, candidly, I’m not going to stick my neck out for someone I don’t know. But the fact that 99% of people DON’T take this approach makes you stand head over heels amongst the pack of other candidates who are just sitting there and putting out resumes.

A ton of AEs or intros via my network to AE’s at companies I was targeting would be happy to help. They get it, they’re living the grind, like we all do. Even the ones that I hit up through cold email/LI message.

More importantly, speaking with AE’s allows you obtain a lot of valuable insight into what’s happening at the company. Specifically things like:

• Are people hitting quota?

• What are the challenges the company is facing?

• What do you not like about the role (though people may be a little filtered on this, understandably so. I’d also reach out to FORMER AE’s who USED to work at said companies to get this insight)

• What’s the team like and what’s (hiring manager) looking for?

• How’s the org breaking out

• How has leadership been dealing with the current economic climate?

All this allows you to position yourself extremely well for that first convo with a hiring manager. This will take longer, but for me personally, it’s a great qualification method to ensure you’re landing in a good spot. That’s the goal.

• Customers

I mentioned this above and this is probably the THE GOLDEN ticket IMO. Having a customer who knows a VP of Sales speak on your behalf and make an intro is fucking amazing.

I ended up reaching out to about 20 former customers from my two past roles. About 10 responded, most of which didn’t get my any leads, but one did make an intro. The story here is great because I was cold emailing both AE’s and the hiring manager at this company.

Once this customer made the intro, I had a meeting scheduled with the snap of my fingers. When I connected to the hiring manager, he appreciated I took the effort to do this and fast tracked me to his CEO for an interview.

Ultimately, I didn’t get the job. The CEO was a little hesitant on my background but did offer to do a one month consult, paid, as a way to see if I was actually fit. I really liked this idea since it was a series B startup and allowed me to mitigate risk for the both of us.

This also gave me the idea of pitching this idea to startups, because at least I would be getting income. Didn’t make much traction there thought since I had leads on other F/T gigs.

Emailing former customers

The key here is that you have to do research when you’re reaching out to customers. When you send an email, don’t ask what companies that they know of. They’re busy, and it’s a lazy question IMO. Instead, go through their LinkedIn and scour their connections to see who/what companies YOU like and then ask from there.

The goal being is that if you have 3 companies you want to get intros to, the customer doesn’t have to think and can quickly respond yes or no. Here’s an example:

Hey (Name)

Hope all is well. It's been a while!

Reaching out since I had left XYZ company and I’m on the hunt to get back into the (your targeted industry) scene.

Thought of you since since you're working with other vendors in the space and have a sense of good products. Specifically looking at (stage and size of company), I've posted some ideas below:

Company X, Company Y, Company Z (to give you an idea). Also open to any others you think highly of.

Lmk when you get the chance and if you can help!

They might not respond right away, so make sure to follow up.

The key of asking this way is they don’t have to think and you can provide them names of people you researched and directly want to get in touch with.

Though many customers responded and wanted to help, only one knew a hiring manager well enough to make it happen.

Reaching out to AE’s who have more experience than you

Take this approach with AE’s at companies you want to be in but frame it from a mentor perspective. I cold emailed a strategic account executive at a large public company asking for advice on his career because he was from the university I graduated from.

He took the time to chat with me and his insights were incredible. He discussed framing my experience, challenges in his career, and plugged me in to the interviewing process with that company and ended up actually introducing me to an employer who made an offer!

The people who are ahead of you in life, though busy, are most likely happy to help. I’ve helped a ton of people who want career advice via cold emails/LI messages. People helped me to get to where I am today while asking for nothing in return. You can leverage that for your job search. Most importantly, take that good karma from someone else that helped you and pay it forward.

Your LI and Resume are Marketing Tools, Use them that way

One of the most interesting conversations that I had with a hiring manager was his feedback on why I’m not a good fit and my LI profile. I used to have everything I did on my LI profile, gaps, and side hustles.

He literally told me, “why do you have this on your LinkedIn, I would just take this out.”

Quite frankly, it blew my mind but he was right.

I took a year to do fitness training and realized I didn’t like it. I blogged and wrote books and had this on my profile. But the reality is that - IT’S NOT RELEVANT.

It also surfaces questions from a prospective employer that just eat up time and you now have to combat. If I was 27 and decided to try something else, why even have that on the resume or my LI profile. Now I have to speak to why I was not selling for a year. And no, the hiring manager does not care that I blogged and made income doing that for a year - what can I do for THEM. And am I dependable, reliable employee. It may be interesting but the point is that I can bring it up in convo, not on a resume or LI profile.

It’s worth noting that this is a case by case basis. Everyone has a story, and everyone maybe have more stints that didn’t work out or gaps they have to explain. The point I took away was that you should be framing this as best as possible on paper.

• Craft and frame your LI profile accordingly

Many people I see have their resume and LinkedIn with a chronological timeline of the jobs that they’ve had. Or put all the jobs that they have and stuff it into a page or two of their resume.

Why?

For example, if am talking to a martech company, my experience for 11 months at IT isn’t worth glassing over. I can talk to it lightly, but the reality is that I had 6 years at one company prior, then 2.5 years for each of the roles prior to those.

• A quick hack I did to frame this was putting years on my LI profile instead of exact dates.

• I also put in quick one liners on accomplishments and what I did to give quick context on audience, company, product, and achievements.

• In my resume, I expanded further with exact dates and time frames, but I just put the length of time (ie 2.5 years, instead of month/year)

People may read this and think that this is not best practice. I challenge that thought process with this question:

• Does a company highlight a down period in their business on their website?

  • Or give a chronological view of performance year over year? (excluding public comanies but that is another story).

    • Of course not!

• Does a hiring manager also talk about all the mistakes they have made on their LI or to you?

  • Of course not!

• Do you talk about all the things that are wrong about you or failed relationships on a first date?

  • Of course not!

The point of all this is that it’s all sales and sales is all about framing. In any of these scenarios you’re putting your best foot forward, from a marketing perspective, and from a personal perspective. There’s not point in shedding light on past challenges in your career , or life, if you have a lot of good things to talk through that are relevant to potential employer. Especially if those challenges just aren’t relevant.

Finally, and this should go without saying but NEVER lie. I’ve talked to reps who have certainly inflated numbers or embellished … not my call to say that is right or wrong but I just don’t do it. You lose all credibility if you get caught and quite simply it’s not worth it. For me personally, it’s just not good standing from a character perspective.

• Get in touch with your network, THEN send your resume

This also might be unpopular or even debated but like I said, after 2/28 I completed changed my process around. For me personally, I was spending too much time on crafting my resume without an intro. Only to have my resume fall into the abyss and wait for weeks hoping for an update.

Most updates I did receive were a couple of weeks out. I had gotten responses within a week for 3 applications out of the 45 which translated into first round interviews.

Comparing the data during the process, and after shifting, the only question in my head was, why am I doing this? It’s eating up time and mental bandwidth when I should be focusing on getting INTERVIEWS.

• A lot of people didn’t ask for a resume until later in the interview process

This is an assumption, but once you have your LI crafted it gives interviewers a good sense of your experience. The rest is a conversation and selling yourself. When you take the approach of getting an intro from their network, you’ve already qualified yourself.

Surprisingly, many companies didn’t ask for a resume until later in the process.

Some did, at which point I’d send over and work on my resume. THAT is a productive use of my time and I’d modify my resume accordingly.

• After networking and getting insights around the company, you can tailor your resume accordingly

The beauty of networking is when you ask questions similar to the ones I’ve asked above you now have insight on how to frame your resume. Key words or stories to focus on. Skills that the hiring manager is looking for. Now instead of a bunch of guesses on whether or not your resume will be a good fit - you have all the info you need to hit all the key points for the team.

• Sometimes you’ll just have to send a resume

I’ve run into this before when going through the process where an AE might make an intro for me and then ask for a resume, before I get to hiring manager. The same happened for other profiles (like partnership managers). Either way, I used resymatch.io and crafted accordingly, because this effort would ensure that my resume has a much higher chance of getting to the top of the pile. That’s all that matters.

It’s worth noting that you SHOULD know how to craft a good resume, and have some sort of boiler plate to modify to a role. It’s certainly necessary during the interview process.

The point here is that people “feel good” when they’re applying, but you and I need to focus on getting actual meetings and interviews. Just like when you’re in sales. Emails with “just following up” or calls at times that you know people are going to be heads down in their days are just doing activity for the sake of doing activity. Meaningful and outcome driven activity is what you need.

You are the product, listen to market feedback

I’ve mentioned before that I’m going to expand on these approaches/stories in another post. But for now the key takeaways are that you need to listen to what people are hesitant about and how consistently those things are showing up.

For example, I came across companies where maybe I didn’t have enough experience closing large enough deals, despite closing massive net new logos. Other times it was I needed a specific background.

Take that valuable insight and either craft a response to it because you know it’s coming or just nail it on the head in the first few minutes of a conversation. If it’s that much of a dealbreaker, get ahead of it so you don’t take 30 minutes your time and a hiring manager on something that will ultimately not end up where you want it to anyway.

When these things happened, I used to get mad and upset.

The reality is that those emotions, while understandable, aren’t effective. I don’t take it personally if a prospect says no to me when I’m pitching a product.

The fundamental mental shift I made was that in this scenario … it is ME who is the PRODUCT. Since I’ve been working at startups most of my career, and like any good sales person - listen to what is being said, take in the feedback, and craft responses accordingly.

DON’T TAKE IT PERSONALLY.

Conclusion

I’m going to wrap this up with another post that dives into some more key insights and stories that helped me shift my strategy on 2/28. The long and the short though is that the numbers don’t lie. Doing the research and hard work UPFRONT led to better companies, more conversations, and higher conversions throughout the funnel.

If you have any questions, feel free to reach out or DM.