Career & Finance

How I Slid Into My (Now) Boss’s DMs to Land My Dream Job


As with many of the best stories, this saga begins at an airport lounge. Prosecco sips were accompanied by scrolling through Instagram stories, admiring friends who were also kicking off the weekend living their best life. It was then that I found myself admiring a beautifully-curated Mexico City series; from a Four Seasons Hotel check-in to Pujol bites to a collection of shiny stainless-steel carry-ons, I was practically drooling.

Suddenly, I found my fingers working faster than my brain, typing, “Stunning! is that a luggage store or some sort of pop-up? the bags almost look like @away luggage – so curious,” before thinking through exactly who I was pinging. Erina Pindar Chamberlain – Managing Director of SmartFlyer and formidable thought leader in the travel industry – was someone I’d looked up to for quite some time. What was I thinking casually sliding into her DMs about bags? Cue, *instant* regret.


Putting Yourself Out There

Little did I know at the time that an opportunity to share her love for Rimowa was a sure-fire way to get Erina talking. With the bubbly fully settled, I found myself really going for it (what did I have to lose, at this point?), replying, “Also, total sidenote, but I just wanted to let you know how much I admire your role with @thesmartflyer. if you ever happen to be looking to expand your team in the social/content space, I would really value the opportunity to chat.” Boom. There was no going back now.

As my heart raced waiting for her response, I envisioned what it would actually mean to make a change; to leave the job that was sucking my soul for a company that was innovative, nimble, and flourishing; to ask for what I wanted and actually get it. No matter the outcome of this chat, I was ready to make a change and actually putting that out there to the universe – despite a fear of rejection – was liberating.


Be Prepared When You Make “The Ask”

When Erina asked for my resume, I had the PDF (which I’d conveniently just updated the night before) in her inbox before I boarded my flight. And as I settled into my cramped window seat, I realized that the conversation wasn’t as random as I’d initially framed it. I’d been working for years to make that ask, not only gaining the experience I needed to toughen up as a young professional, but pitching and executing projects that provided a portfolio which I was proud to present. It just took my subconscious to take over and remind me I was qualified.

Beyond the line items on my resume – an obvious prerequisite to landing the job – this wasn’t the first time I’d engaged with Erina via Insta. And fast forward months later, she was sure to remind me that the only reason she responded in the first place was that my name wasn’t completely random to her; it was a reminder that working up the courage to make the ask is only one piece; you’ve got to lay down the framework first.



Be Willing to Make a Change

After a month of painful ghostly silence (these things take time and diligent follow-up!), I was interviewing in the SmartFlyer HQ office. Nerves aside, we clicked. FaceTiming my mom through happy tears to share that I’d been offered the job as Marketing and Social Media Manager on the spot – one which was never listed as open in the first place – was one of the most gratifying moments of my career thus far, even if it meant being that girl that was happy crying on the subway platform.

By Monday, I’d given my notice, and by Tuesday, I found an apartment in New York City. Two weeks later, I was on a flight to Vegas to begin my new role at the luxury travel industry’s biggest annual conference, Virtuoso Travel Week. It was a whirlwind start – one which some would call trial by fire – but I wouldn’t have had it any other way. When you put that kind of energy out into the universe, you’ve got to be ready for it to manifest in tangible ways.


Know Your Audience and Lay the Groundwork

Looking to pursue a new job opportunity? Let’s start with the obvious. Sliding into a decision makers’ DMs at your dream company may not always pan out, but that doesn’t mean there aren’t other opportunities to be creative and get noticed! Do your due diligence and learn more about the leadership team on a personal level. Engage on LinkedIn. Send a handwritten note sharing your interest in being connected. Establish authentic relationships with people in their circle. Make it your mission to have them know your name for all the right reasons.

At the end of the day, people want to work with people they like, know, and trust. Consider all the potential touch points – both digital and in-person – and be mindful of how you’re building yourself up. As a Social Media Manager, this means that my Instagram is an extension of my resume. But perhaps you’re in sales, which means your social currency may come in the form of being active on the networking scene. No matter what, be sure you’re always painting the picture of someone who’s not just easy to work alongside, but interesting to be around.


 No matter what, be sure you’re always painting the picture of someone who’s not just easy to work alongside, but interesting to be around.


Get Comfortable with Being Uncomfortable

It sounds like a cheesy line from a motivational speech (probably because, well, it is) but the ability to sit in stress, anxiety, and fear is so important. If you want to make a change, you have to be willing to put yourself on the line and take a risk. You must put aside your ego and be OK with rejection. But one thing is for sure: vulnerability will manifest into something beautiful in ways more profound than you’d ever believe. Do the work, make the change, and never look back.