Dillon McDermott has worked in the SaaS world for 13 years, mostly leading sales and other go-to-market teams. He’s a Boston native, and currently resides in South Boston, but spent 8 years in San Francisco. Recently, he was VP of Sales for Thankful.ai, helping to grow new business sales and leading the company to an acquisition in July. Prior to that, he led the North American sales team at SurveyMonkey, focusing on their CX and Enterprise Solutions products.
This one’s for the job hunters. There’s a lot of you out there – myself included until recently!
Here’s a fun stat – in 2023 there have been over 240,000 roles eliminated in the tech industry (per MorningStar). This has impacted more than one thousand companies…and we’re not even through Q4 yet! 😬
The market can seem bleak, and on top of that the hiring process is often grueling. Fortunately, as companies plan for 2024, hiring is inevitably picking back up. But man, it seems like lots of companies are spooked! I mean, execs are fresh off of a few quarterly board meetings where they’re justifying another missed forecast, reviewing the impact of their latest RIF, and talking more about operating efficiency than growth multiples.
No one wants to misstep, and the so-called “growth” companies have switched out their hockey stick charts in favor of cost reduction techniques (or, penalty kill strategies to stick with the analogy?).
So where does that leave job hunters?
Well for starters, enough with the doom and gloom! One of my biggest operating themes, and certainly one I carry into a job search, is STAY POSITIVE. The process is frustrating–plain and simple. And while rejection will outweigh success in this chapter, it just takes one! To lend a hand, I thought I’d share a few tips that have been helpful for me during the job search:
- Stay Organized
Maybe it’s been drilled into me from a decade of sales management, but I manage the job search like I’m managing a pipeline.
- I’ve got my CRM (Google Sheet) of prospects and have it all broken down by company profile and key details: HQ location, employee size, funding, compensation, stage of the process, key stakeholders, and, of course, up to date next steps… old habits, ya know?
- And yes, much like sales, you’re going to lose plenty of times. The key thing is what can you learn from a loss? It’s always helpful to step back and analyze what you think went well, what could be improved upon and how you can better prepare next time.
- Ask for feedback! Any decent hiring manager should provide you with some constructive feedback that can help you out moving forward.
- Leverage AI
Of course you have! Seriously though, ChatGPT and other freemium AI enabled tools are a secret weapon in the interview process. Some future company will make a killing with an AI-fueled career management platform…startup idea? 🤔
- ChatGPT is helpful for refreshing the resume, building email templates for outreach, coming up with some compelling interview questions, etc.
- For example, a prompt you could use to help nail that marketing gig could be “Provide a list of 10 strategic questions when interviewing the Director of Marketing for a SaaS company.” Have some fun with it and test things out. You’ll find some good ones! But, make sure you’re genuinely interested in the answer or discussing the topic in depth.
- Look for other freemium tools that will help you be more efficient with the process too – email address finders, company news/funding stories, Google alerts for companies you’re interested in, BuiltWith to inspect what tech the company has just to name a few.
- Stand out from the crowd
I saw a stat that said 80% of interviewees don’t send a follow-up / thank you email. This one is just TOO easy.
- Make sure to send a brief but thoughtful note to your interviewers. But, this isn’t just to show face and say thank you. Use this as another opportunity to show your stuff. In your message, make sure to share specifically what about the conversation that fires you up about the role/company, offer something that may have pleasantly surprised you, another question you didn’t get to, or some third party info you found that ties back to a part of your discussion. Trust me, not many other candidates are doing this and it will immediately set you apart.
- Go the extra mile. Let’s be honest, as job hunters, we have the time! If you discussed some of the responsibilities or objectives for the role, it’s a great opportunity to showcase what you know. Is building a hiring plan important? Setting up a strategy for a customer expansion strategy? If you’re truly qualified for the role, and know your stuff, put together a simple plan, an example of how you accomplished a similar task/project before, or a few bullets on how you’d approach achieving those targets.
- Get yourself plugged in!
- There’s some great communities out there for job searchers. Of course, for folks here locally, MGMT Boston provides an incredible network. I tapped into the network for my search and was referred into a company I interviewed with.
- Other online communities on LinkedIn & Pavilion (for GTM folks) are great outlets as well
- Reach out to the ones pulling the purse strings! Many VC firms have a talent team for placing candidates into their portfolio companies. Same goes for PE firms. I’ve worked with recruiters from companies like OpenView and Craft Ventures who have looked to match me with relevant opportunities within their portfolio.
- Find your communities, and be active. It’s no secret you’ll find more success through your connections than firing off application after application on company job boards.
- Find other sources to pour energy into
- A lot of people say searching for work is a full time job. In general, I try to approach it that way. But hold up…give yourself a break!
- I found that having some outlets to tap into your creativity, expend your energy or dedicate some time to is truly beneficial. Doesn’t matter what it is, but X out of the resume and close the laptop. Your mental wellbeing will thank you.
- For me, getting outside and running has been my go-to. Most days I’m out looping around Castle Island in Southie or the Esplanade.
- I’ve also never been much of a reader in my adult life. But, I’ve been reading a book every couple of weeks and it’s a habit I’ll be taking with me in the future. My most recent read was Dennis Lehane’s Small Mercies – a great one for the group here in Boston who are into crime novels!
Finally, if I can help in any way let me know! If you need some help with interview prep (I’ve done a lot of them recently), resume guidance, introductions to folks in my network or just some general career advice just shoot me a note. I’d love to chat!
Best of luck,
Dillon