In this episode: Michael Gagliano, Head of Sales (SMB) at #paid, joins us to share his progression through tech. What surprised him most about sales coming from a traditional marking background and education? How does working at a large sales team differ from a start-up? How can you leverage your time in school to help with business acumen? All that and more next!
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In this episode: Michael Gagliano, Head of Sales (SMB) at #paid, shares his progression through tech. What surprised him most about sales coming from a traditional marking background and education? And more!
Welcome to sellers journey, the podcast where we speak to great sales reps and leaders and share their real stories from start to sales success.
Joseph Fung: Hi everybody, I’m Joseph Fung, and today we’re speaking to Michael Gagliano, who’s the Head of SMB Sales at #paid. And today’s gonna be a fantastic conversation because Michael is also a fantastic Community Builder, as well as a Startup sales coach and has had such an incredible journey. Michael, thank you for joining us.
Michael Gagliano: Absolutely, Joseph glad to be speaking with you today.
Joseph Fung: Now, Michael, I’ve had the good fortune of seeing some of your fantastic work firsthand. Your work co-organizing sale CEO, your work with Startup Laurier, these are all fantastic endeavors. But maybe you could help our audience get to know you better. First and foremost, #paid. What is it? Can you give us an elevator pitch?
Michael Gagliano: For sure, I’ll keep it short and sweet. So we’re a Toronto startup and direct to consumer brands like your Casper or Native Deodorant. They turn to #paid. And our platform to scale their influencer marketing programs. So we have a network of thousands of creators, vetted, social content creators, and we match the most relevant creators to those brands for them to scale their influencer marketing programs through our platform.
Joseph Fung: Now, I have to ask I know this isn’t a show about pitching, but we do have a lot of entrepreneurs, solopreneurs, small business owners who listen in. is this a service primarily for large businesses like deodorant makers or does it work as well for smaller enterprises?
Michael Gagliano: So the team that I lead it’s a team we launched about eight-nine months ago, specifically for small businesses. So most of our customers in that space are really small, three employees, five employees, ten employees and so we’re really building a platform tailored to small businesses and startups. Where they can scale influencer marketing without having to build a team like you’d find headed ITA’s. You know with a 15-person influencer marketing team. So I’ve seen as small as a one-person company of CEO using our platform. And I have been getting some great results-driving purchases of his product on e-commerce. So that’s been awesome to see.
Joseph Fung: I am so looking forward to our conversation and kind of following that journey all the way to your head of sales role. Because I’ve got some questions, I want to get to on that. But, let’s rewind let’s kind of go back to the beginning. Where’d you grow up? Where did you go to school?
Michael Gagliano: For sure! So I grew up in Toronto and then in first year moved to Waterloo and attended Wilfred Laurier University. So I the School of Business and Economics that honours undergrad in Business and specialized in marketing there. And I think that’s where I fell in love with the tech community, and you’ll know this with your time in Waterloo. But over the last ten years, it’s been amazing to see what’s come out of Waterloo. And so I got to spend about five years from 2009 to 2014 being involved and getting immersed and creating a passion for tech in Waterloo.
Joseph Fung: I love it because you know when we look at your journey, that enthusiasm for tech is so evident and being steeped in it myself. I think it’s the best place to start. But, startups aren’t the only place. Your first role out of school wasn’t really at a Startup. Was it? Maybe you could share with our audience; you know your time at Microsoft? And what that role was like?
Michael Gagliano: For sure so I got to spend my last two co-op terms at Laurier with Microsoft in Mississauga, and that was my first marketing role. I thought that you know over the last few years at that point, I wanted to be in marketing, I got to be a part of a really exciting team and launch products like windows eight and the new phone. And so that’s I think, where around that time, where I really knew I wanted to be working full-time at a tech company. And shortly after I finished there, I had one last term at Laurier for the summer term, and then I graduated.
And at that point, I knew I wanted to be at a tech company, but I also knew that a large company wasn’t for me. I found that it was a little bit too slow to get decisions made, I wanted to have more ownership more accountability and so around the beginning of 2014, before I took my first role at Uberflip, I was considering moving to San Francisco. And so I one night I just woke up I booked a ticket to San Francisco by myself and started finding interviews at a bunch of different tech companies there. Around the same time, I had been interviewing at Uberflip. And actually was interviewing for a marketing role because I knew nothing about sales, never heard of an SDR. And so I ended up passing on an opportunity in San Francisco to join the team and build up sales at Uberflip.
Joseph Fung: Okay, so let me get this right. You wake up, decide that maybe you don’t want to be at a big company. So, your next step is to buy an airplane ticket to San Francisco. Did I get that right?
Michael Gagliano: Pretty much. I took a little bit of a risk. I slept on a friend’s couch for four or five days. Interviewed at a bunch of different companies and then came home and made my decision around what was going to be my first full-time role.
Joseph Fung: Okay now for some people this might sound like a completely irrational decision. But, you know I mentioned earlier you spent some time with Startup Laurier, and in that context, this makes complete sense maybe you can help our audience understand, what is Startup Laurier? And you know what was your role in co-founding that organization?
Michael Gagliano: It was, it’s an organization that is still running today, ten years later something that I’m very proud of actually and we saw myself my co-founder Anthony, and I saw a great opportunity at Laurier within Waterloo for Laurier students not just business students, art students, science students, kinesiology students to contribute to the entrepreneurial community. And so we spent a lot of time in the first couple years of our undergrad, meeting people at the University of Waterloo, which was just thriving with the Startup culture with programmers, engineers, people developing companies. And we didn’t see that same spirit at Laurier, and there was no clubs really focused on entrepreneurship.
And so we launched Startup Laurier for the first year to our name was Laurier innovation and technology club. We rebranded to Startup Laurier, and we launched it to support Laurier students to bridge the gap between tech and business. And to help them to launch their own company. So, we did some great events. We ran Entrepreneurship competitions. We brought on companies like Google and Facebook for the first time ever on Laurier’s campus, and from that, we helped a lot of students launch their own companies give prize money, and there was a lot of fun, and it’s awesome to see ten years later it’s still operating and every so often if winning Club of the year. So, I definitely stay in touch with the group there.
Joseph Fung: So, I think given that experience I mean the contribution to the community is huge and so I can really see how you found that role as a community builder and your role in marketing at Microsoft I think makes a lot of sense. You know given the education what was that interview process, like at a Uberflip? You know what had you switch from looking at a marketing rule to looking at a sales role there? Because that must have been a deliberate decision at some point.
Michael Gagliano: Yeah exactly! I think this is something that I’d love you to share with your listeners because it taught me that you can go into an SDR or sales role with any background and any experience. If you have the right mindset and are willing to learn and put in work. And so right around that time my last month or two at Laurier, I decided with a couple of friends to launch a Kickstarter project. We had never done one before, and we launched the Kickstarter called Wise Words where we design 40 unique cards. And they had people like Mahatma Gandhi, Mother Teresa, Albert Einstein, Michelangelo and some of their best quotes. And so we did a fundraising campaign where we were looking for 6k.
I think we did a hundred and forty percent of our goal. And right around that time was when I was interviewing at Uberflip, and so I went into that interview for a marketing manager role. Because I knew I wanted to be in marketing. I told the founders and the Head of Marketing about my Kickstarter program. I actually brought one of our products in to show them and leave there, and they asked me, they said, “we think you’re a great culture fit for our company. May you don’t have the right skill set for this inbound marketing role, but, have you considered sales? And we are just launching and hiring our first SDR team. And we have a Director of Business Development who’s launching that.” and so I said, “what’s an SDR? What sales? I really didn’t know anything about it.” and they saw that you know and they told me this, “if you’re able to drive thousands of dollars of sales of a of a card business to 30 countries around the world you know you can sell our software.” and so I met with the director, I learned about the SDR role and I took the plunge, joined as the first SDR, and there wasn’t much of a playbook, so it gave me the opportunity to really learn by doing, and so it was like a lot of us that go into sales, we kind of accidentally get into it and I haven’t looked back since.
Joseph Fung: Okay! So, you determined Uberflip, if you look at the kind of LinkedIn bullet points, it reads almost like a cliché like SDR one year, AE the next year close a million bucks Enterprise AE. I mean it sounds almost archetypal but, I’m sure there were surprises in there. You know what were some of the wrinkles? Or what surprised you about that journey at Uberflip.
Michael Gagliano: For sure, it was a great success. I was there just under three years but like like I said when I joined you know I was the only SDR and so we had one or two AEs at the time and it was quite hard to learn what to do, how to do the job. And so I remember back there are days where I would just have a long list in Excel of people’s names and phone numbers and just start calling alphabetically and get you know rejected 100 times in a row, and I think that experience and having and finding some mentors along the way listening to audiobooks, reading podcasts, helped me to figure out what to do. So, there was a lot of rejection a lot of figuring things out figuring out what should our pricing model be. We started off with $50 a month price point. When I left Uberflip you know, we were selling deals at 5,000 a month. So, to figure that out along the way was an amazing experience. A lot of challenges and mistakes. But, I think that first year of just grinding and hustling in that SDR role to create meetings, to create conversations gave me the best foundation for the next six years.
Joseph Fung: So, I’m gonna speed up and go kind of zoom for a little bit because I know you moved on and you picked up a team lead role, a sales manager role, all of these in quick succession, and now you’re that the Head of Sales at another company. So three great tech companies, you’ve got all this responsibility. When you look back at your journey, you know how do you apply that in your hiring? You know how has your journey informed the way you hire now at #paid?
Michael Gagliano: I think for one thing not having any biases around someone’s background. And when I moved into my first manager role, at Shutterstock, I had six or seven other peers in sales manager roles. And I was definitely the youngest of the group. I think at 26 or so at the time 26-27. And so right now when I’m hiring whether it’s supporting to hire SDRs or AEs really keeping an open mind about people’s backgrounds. And even not caring if they come from a sales background. And I think I’ve seen great successes people going into SDR roles coming from all sorts of different previous experiences. So what’s more important to me is that that person has the right mindset, but has some track record of success. So I’ve seen SDRs as successful SDRs come from restaurant server backgrounds. There was one at my previous company, who was an Olympic swimmer and finished her athletics and came into an SDR role. And that was somebody that practised and worked consistently at something for ten plus years. And had that perseverance and passion. And so those are some of the things that I look at and seeing how quickly I grew from my first SDR role to my current role in about seven years just having that open mind for every sale hire that I interview.
Joseph Fung: Wow! And as you had reflected and keep that perspective in mind, I can imagine that advice resonating not just with the people that you hire but the broader community. So, if we think about that experience now that you have translated. What would you think are some of the biggest lessons you picked up along your journey?
Michael Gagliano: I’d say two lessons. So, one is really leveraging, linked in, and building your personal brand and it’s something that I’ve invested more into over the last while. I’d encourage anyone starting off to build your brand today and to invest time to post every day on LinkedIn to build a community around yourself to engage with people to build a personal site and to get active on Twitter as well. I’ve found so many opportunities from Twitter and LinkedIn, my second startup, I found out about them as the co-founder reached out to me on LinkedIn. And so I’d say building your personal brand is so incredibly important.
I just last week put up a new banner on my profile and want to take advantage of that real estate. I think the second piece of advice I’d have is around leveling up when it comes to learning and writing as well. And so I think I learned the lesson about writing over the last little while. But, I would say that keep practising your writing and writing on social selling writing a LinkedIn post, writing blog posts, that goes into building your personal brand. And then never stop leveling up whether that’s finding relevant podcasts. I just wrote a blog post a couple of weeks ago about scaling up and scaling up during Covid 19 is a great time with so many free courses online right now. So, I think this is the perfect time to level up and learn some new skills and practice your writing. So those are a couple of lessons that I’d leave people with.
Joseph Fung: I love the fact that you mentioned those the idea of leveling up by listening to podcasts as we speak about that on a podcast. Clearly our audience is ahead of the curve in terms of meeting your goals. So, I love that. If thinking a little bit about all these lessons, there’s such a wealth of information there. And I’d really like to deposit our moment to highlight for our audience that Michael is so accessible and has such a great wealth of experience that he’s really worth reaching out to and following on LinkedIn, his involvement in the community because there’s just so much knowledge there and he’s really exemplified that idea of an accelerated journey through sales. So I wanted to do a quick shout out there. But, Michael you’re still early on in your journey, and there’s still a lot of runways ahead of you. So, would love you to cast your eyes forward. Where you are heading? What is on your bucket list? Whatever cliché you want to think of, what do you aspire to still accomplish?
Michael Gagliano: I think that the first thing on my list there is building my own business and I’ve gotten to help create and scale up three different startups now and some larger companies before that. And so, I think being able to create something from scratch, test the initial hypothesis, find our very first few customers and operate outside of sales as well is something that I’m very interested in and starting to put some thought into in terms of different you know side hustles and ideas. I, one of my first articles that I wrote this year was about living a Polymathic life.
And so one of my goals over the course of my next 60-70 years really looking long-term is to become a deep generalist and a polymath is someone who is, someone who has mastered at least three different domains. So, I’ve been over the last few months very interested in data science and AI and starting to add a second discipline that I can add a lot of value to and build with. So, I think those are a couple of things that are top of mind for me, building my own business and becoming more of a polymath or deep generalist. As I become an operator not just from sales as a sales perspective but from all of the different aspects of running a business. And also embracing the arts and the creativity as well. So, those are the two main things that I’ve been thinking about.
Joseph Fung: So, for what it’s worth, Michael, you said adding a second discipline, but I’d argue you’ve already added two at least two when I look at your experience on the Alzheimer Society board co-organising sales tio, Startup Laurier your ability to deliver as a community catalyst. I’d say it’s already a second discipline there. So, make sure you don’t sell yourself short there. Maybe the kind of AI and a science degree is more of the third than just a second.
Michael Gagliano: I appreciate that!
Joseph Fung: Now I know I said we wouldn’t keep you too long and I want to stay true to that. But, can I ask a couple of rapid-fire questions before we let you go?
Michael Gagliano: Shoot! Let’s do it!
Joseph Fung: Cool! Okay, you’ve been in a ton of companies, you used a ton of tech, what is your favorite sales tool?
Michael Gagliano: Without a doubt, it’s gotta be LinkedIn. Not even necessarily navigator, just plain old LinkedIn has been incredibly valuable for a couple of the reasons that I mentioned. Not only for building your own community or your own influence. But, just adding value to prospects and to people’s lives. And so there’s so many opportunities from LinkedIn. If they made me pay for it for the general license, I would pay for it, it’s so valuable.
Joseph Fung: Well, you got to be careful that hopefully, the team from LinkedIn doesn’t hear this. Because you might give yourself an invoice.
Michael Gagliano: Yea! Exactly!
Joseph Fung: Movies, films. What’s your favorite movie?
Michael Gagliano: I got to go back to the 70s and say “The Godfather – Part 1”. A great classic favor for a lot of people. But it’s one of my favorites.
Joseph Fung: Nice and if you cast your mind back to your earliest days when you’re a kid, what did you want to grow up to be?
Michael Gagliano: An architect! I always loved real estate and buildings and architecture. And so it’s something that I eventually want to be able to invest in or be a part of, just creating buildings in architecture. So, that’s something I thought about early on.
Joseph Fung: As a Community Builder and a catalyst that doesn’t actually surprise me. What a delightful answer! Thank you!
Michael Gagliano: Of course!
Joseph Fung: Michael, this has been great. Happy to have you on the show, happy that we had this conversation and I’m so excited to be part of your journey and see where you led next. Thank you for your time and sharing today.
Michael Gagliano: My pleasure, Joseph. Appreciate you having me on and excited to stay in touch with you.
Joseph Fung: Absolutely, I’m looking forward to our next conversation. I hope you have a wonderful day.
Michael Gagliano: Thank you!
Joseph Fung: Take care! Ciao.