Ask A Recruiter - Tech Start-Up Huckleberry

Cole Feldman: I'm the Head of Sales at Huckleberry Insurance.  Our organization is an insurance startup.  We’re specifically focused on small business insurance. And there are two products that we mainly sell, which are workers’ comp and general liability.  Something important to know about workers’ comp, and the reason that it gives us an advantage to be working on this product, is that it’s mandated by state law for small businesses in most states.  One of the states where it's not mandated is Texas. And there are a couple other states where it’s government run, it’s not privately run, that we don’t operate in. General liability is compulsory as well in cases where you have a landlord  or a contractor requiring  the insurance.  Those are the details that give us a strong business position. And the reason that the space is exciting to us is there are a ton of really exciting, insurance-type businesses that are doing really well right now. Most people have heard of Lemonade, which is a personal insurance startup.  And then there’s Hippo for home insurance and Metromile for car insurance.  A company that is similar to us, Next Insurance, just recently raised a quarter million dollar round and hit unicorn status.  So basically we’re operating in a space where venture capital money has a lot of interest right now, which is insurance.

Career Services: And what is it that makes Huckleberry a great place to work?

Cole Feldman: So we have 20 employees and when I joined I was employee number 6. And that's not for everybody.  Especially coming out of college you might want a larger company or a more stable, steady job, which is not necessarily what startups are about.  And so to answer your question more directly about what makes it a great place to work is you definitely get the startup feel. We're backed by top-tier venture capital firms, a lot of the people that work at the company have experience working in startups, they have very scrappy ownership mindsets.  And they're also very smart, ambitious people that are brought on because they’ve had a lot of success in their previous roles. So I guess to put it in a list:

  1. Working for a top tier startup, working on an important problem right now is very exciting. 

  2. Working with very smart, ambitious people.

  3. We do work hard and we like to have fun.  For example, after we raised our Series A round at the end of last year our CEO flew the whole company to Las Vegas for the holiday party the next week.  

So I think if I were to summarize what makes Huckleberry a great place to work: it’s the combination of this work hard aspect of being at a tech startup with 20 employees where you’re gonna have a lot on your plate, but then the fun aspect  when you experience success you get to do things like fly to Las Vegas for the holiday party.

Career Services: What advice would you give to students who want to break into the tech field and a non-technical role?

Cole Feldman: I encourage you to think first what size company you want to join. If you want to join a company like Google or Apple or Amazon they’re hiring across finance, accounting, operations, HR, sales - you can do anything. But if you want to join a tech startup you have to think about the types of departments that get hired into first if you want to be early. Oftentimes other than engineers, sales people are going to be the first people hired at a company. Because once that company has their product-market fit, they need frontline soldiers to bring that product to consumers, and that’s when salespeople get hired. And the other thing is operations. So “non-technical” is a really big umbrella term for anything a company needs to do to keep the train running that the CEO or the engineers don't have time to do. So maybe that’s answering customer success calls or doing Excel projects that the CEO doesn’t have time to do, or keeping our data clean. 

So for the tech startup perspective, for the non-technical roles I would be thinking about sales and operations. The way I would decide between those two things would be: how much of a people-person versus a project-person are you?  If you’re the kind of person that can just put in their headphones and work on Excel all day, and be at their computer working on longer term projects, look for operations roles.  If you love people, you love talking, you majored in Communications or Sociology, or even if you didn’t major in those things but you still like talking to people, I’d look for a sales role.  

Career Services: What would you say is the most common mistake that you see internship candidates or new graduates make during the interview process?

Cole Feldman: There are a lot of mistakes made early on. I would say the first place that mistakes are made is in messaging with a recruiter or hiring manager at the company. And that often is going to take place on LinkedIn or email, maybe Handshake.  If you mess up your grammar, or don’t have complete sentences, or misspell a word, usually that's a knockout for some companies.  Not necessarily because of the lack of skill, but because of the lack of attention and care to use something like Grammarly or look up the spelling.  I think that’s the most superficial knockout that happens earlier on.  

Other than grammar and spelling the second part of messaging with a recruiter or hiring manager is just be super polite and humble and excited. I think there are a lot of candidates that we’ll knock out right away. Culture is a big thing for us, and humility and a non-entitled attitude are big for us. So if the recruiter can tell that you're not taking it seriously, or if a recruiter sends you a long message and your response is “What’s the salary?” you're probably not going to advance further in that process. And there are various other mistakes that can happen at a phone screen stage, at the video interview stage, and at the onsite stage.

Career Services: Can you expand on mistakes that are made in the initial screen phase whether that's a phone screen or being done over video conference?

Cole Feldman: For my Account Executive role, I will often do a phone screen after messaging. That phone screen is particularly important for an Inside Sales role because the way you perform in the sales function is you’re talking on the phone with a client.  So I want to know, can you build rapport right when you pick up the phone? Can you talk about something other than the job or the interview right away? Maybe the weather or what's going on in the world or even make a joke and have a natural conversation.  And then after that for the resume check it’s either a fit or it’s not a fit.

In a sales interview, it's hard to kind of fake your way through. For example, when we call candidates that we expect to have sales experience, because they either have a sales internship or sales role previously I’m going to ask questions like  “How many dials per day were you making in that position?” and “How many emails did you send?” “How many deals did you close?” “If you didn't close the deals, how many deals did you help close?”  If your answers to all those questions are something like “I made 4 dials per day, I didn’t send many emails, and I didn't actually close any deals”, then it doesn't matter how well you tell that story - you didn't do the job, which is the experience that we're looking for. There's a certain amount of “fit” aspect where it’s just there or it’s not. Overall, for a phone sales role, how you conduct yourself on the phone is most important.  

Career Services: In hindsight, what advice do you wish someone had given you as you were starting your career as a new professional?

Cole Feldman: Start earlier. I've been working professionally since I was a senior in high school when I started interning for a private wealth management firm.  There's so much to learn just working a job. I think the way to crystallize the advice is you can’t start early enough. And what that means for students is to get an internship.  I think especially sophomores or juniors, if you have the option of going home and working at the restaurant you’ve been working at for 3 years or stocking a warehouse or working on a farm, which are all legitimate things - I worked at my Dad’s construction company and I worked for restaurants and I worked on a farm - but if your aspiration is business or working in an office or working in tech, go get an internship in any of those fields.  You want to be in finance?  Go intern for a finance firm-filing papers, it doesn’t matter.  Do you want to work in tech? Find the scrappiest startup that’s willing to hire a junior intern and take a chance on you.  It doesn’t matter what they want you to do.  Even if you’re just cleaning data all day you’re going to learn so much being in that environment.  And that CEO you meet that summer is going to connect you to 5 CEOs when it actually comes time to look for a job. 

Career Services: If students aren't able to get internships over the summer is there anything that you would encourage them to do to keep building their resumes?

Cole Feldman: Due to the recent COVID-19 situation, getting an internship during the summer is going to be very hard.  But if I could give you advice outside of the recent situation, really work hard on getting an internship.  Especially from a sales perspective, the process of getting an internship is like a sales job in and of itself. You should have 100 different companies in an Excel sheet, you should have the contact person for all the recruiters, you should be calling them and messaging them multiple times a day until you get in touch with somebody and really work hard at getting an internship. If you absolutely cannot get an internship, then find a way to get real experience.  There is only so much you can learn in the classroom. And for sales, especially, you can't learn sales in the classroom. You have to learn it by doing.  So if you have a side hustle or your own business that you’re running, then work on that side hustle to get more experience in business or sales, or if you want to get into a technical position down the road, then start working on your own technical side projects. 

Career Services: Any final advice or other information about Huckleberry that you’d like to share?

Cole Feldman: Our vision at Huckleberry is to simplify insurance for small businesses. In a multi-trillion dollar industry where paper forms and fax machines still predominate, we aim to rebuild small business insurance from the ground up by reimagining how you procure and manage insurance for today’s digital business environment. We're backed by Tribe Capital, Uncork Capital, Crosslink Capital,, Postmates CEO Bastian Lehman, Apartment List CEO John Kobs, and several others. We recently raised $18m in Series A funding.

We are hiring and looking for talented individuals across our organization. Check out our current postings on our careers page:

You can also find me on LinkedIn by searching my name “Cole Feldman.” Feel free to send me a message!