The Top 30+ Questions Candidate Ask about HubSpot

Katie Burke
22 min readJan 18, 2022
Our amazing team in Colombia connects with each other and their families.

One of our core beliefs at HubSpot is in democratizing information. Doing so was part of the founding philosophy of the company with inbound marketing, and it’s also imperative to our commitment to DI&B. Last year, I put together the Ultimate Informational Interview outlining consistent questions our recruiters get about life at HubSpot. This year, I’m answering the top 30+ questions I got from people on LinkedIn. In the wake of HubSpot’s recognition as the #2 Best Place to Work by Glassdoor, I hope this helps candidates considering HubSpot learn more about us in a way that is accessible to everyone. So let’s jump in, shall we? Thanks to everyone who submitted questions!

What does “cultural fit” look like to you? How important is it for you to hire candidates who fit culturally well at HubSpot? Do you think it’s sometimes important to hire who may not fit culturally well but could bring new ideas into the company? At HubSpot, we think about culture add versus culture fit — the best people make our organization better versus fitting any sort of mold. A few things that might be helpful for context as it relates to culturally additive interviews at HubSpot:

  1. Our culture is predicated on autonomy so we are actively looking for people who like working independently but also highly value collaboration and transparency, so think about examples of when you have exhibiting autonomy. To me, autonomy has nothing to do with level or experience — if you’re working in retail, you can exhibit autonomy to adding personalization to an order or going the extra mile to solve for a customer or innovating on a new process and approach to help people that you share with your coworkers. So if you’re thinking of examples, focus on picking things that are real versus trying to impress your interviewer with a corporate example.
  2. We often refer to HubSpot as a teaching hospital — we really value growth mindset and folks who value feedback and are always seeking to get better, so consider how you lead with learning and growth in your own life or current career path as you think about the role you’re applying for.
  3. We value people who make our culture better versus who aim to try to fit it — our new hires in the last year have pushed us with great ideas and input on hybrid culture, brought in concepts from other companies that can make ours better, and shared traditions that they are adopting within their own teams. As an example, we had an event in November to learn from our VP of Central Strategy and Operations, Chris Hogan, that was entirely generated by a team lead on our recruitment suggesting a concept she had seen work well at her previous company. The best people add to our culture, not fit it, so I hope this helps for clarity on how we think about it here.

Thanks for putting yourself out there. What’s next for HubSpot? We have a new CEO in Yamini Rangan, a new Chief Product Officer in Stephanie Cuthbertson, and a new Chairperson (our former CEO) Brian Halligan, so I think there is a lot to be excited about ahead. A few things in particular that I’m excited about: 1) Our global growth — we just starting hiring folks in the UK and Canada (Ontario), and our global business is humming, so there is a bunch more opportunity to be the CRM of record for SMEs globally ahead. 2) Payments and Operations Hub — our product team is, as Brian Halligan says, on fire, and they are building truly remarkable products — Operations Hub Enterprise and Payments are our newest addition to our offerings, and I am super excited about growing those businesses alongside our existing CRM, Marketing, Sales, Service, and Platform plays. 3) Speaking of Platform, we want to help millions of organizations grow better, and doing that means we need to not just build a great product but also be a great dance partner within the broader ecosystem. So in addition to our product platform plays, I’m excited about our HubSpot Ventures Fund focused on the CRM ecosystem — the companies we are investing in are remarkable, and we are honored to support their growth! Then for our culture, we have a lot of global growth ahead, we’ve doubled down on hybrid, so excited to lean in there as we grow, and we also released our first Sustainability Report, so lots of exciting ESG work ahead for us, too!

Our new Chief Product Officer, Steph Cuthbertson, with some awesome POPS and product folks in our Coffee Garden.

I’ve applied to HubSpot a bunch of times and never gotten an interview, how do you recommend breaking through? First, just want to acknowledge that getting a rejection note from a company stinks, and I’m sorry you experienced it. And, I would also just say that while I adore HubSpot and think it’s amazing, a job doesn’t define your success, so don’t let it get you down. But getting down to brass tacks, a few tips and tricks that I hope help: 1) don’t boil the ocean — we really recommend that folks target a maximum of three jobs versus trying to apply to 8 roles, so pick a few roles and really lean in there. 2) take a look at the career journeys of folks focused in the roles you’re interested in. We often host recruiting events featuring different teams, watch or read the transcript to find helpful examples or context to inform your application. 3) Leverage HubSpot Academy — part of our approach as a company is to give away content to help people grow. Academy courses are free and can help you learn our product and our platform and a bit more about our company, so I recommend taking advantage of it if/where possible. 4) I would also just say that working at HubSpot is great AND that there are a bunch of incredible solutions partners and agencies globally that have wonderful cultures and that use our products to grow, so check them out in parallel too. 5) Take a breather — if you get declined a few times, take a month or two to recharge and plan your approach for take two. We have many people at HubSpot who have joined after several rejections and have thrived at HubSpot, so you’re in good company!

How does HubSpot help employees prevent and battle burnout? Are these initiatives helping? You can read more about the initiatives we announced here, and I would say yes they are working so far, but we aren’t done yet ensuring that our employees get the balance they need to balance life and work. When you’re a fast growing company, this isn’t a one and done effort, it’s something that requires constant fine-tuning, and we are really committed that work.

Where do you see HubSpot as a company in next 3–5 yrs? (Biranchi a software engineer who just joined our team asked this in the fall prior to joining us.) First, congrats on your offer Biranchi, so glad you’re joining us! In 3–5 years I suspect that we’ll be in even more global markets than we already are now — the SMB/SME market globally is significant, and I really believe we are just getting started with our international impact at scale. Excited to see your impact here!

A question I’m interested in seeing an answer to is how HubSpot thinks it can further encourage applicants to overcome the obstacles of confidence gaps and imposter syndrome? I see the company avoids using (‘overly prescriptive’ to quote you) details in the job description that may hinder some applicants, but I’d also love to see a step that goes beyond telling people with imposter syndrome, to just not have it. Something less abstract. I appreciate this can be time consuming and tricky, and will differ based on the role being hired. In content related roles, maybe a link to an existing blog/document/piece as an example could make the description seem more tangible. I appreciate the sentiment behind this question, but also think telling people not to feel imposter syndrome could feel dismissive to their lived experiences, so instead what we try to do is make our job descriptions clear, include a CTA with a clear and compelling callout to not let confidence hold you back from applying, then democratize as many resources for candidates as possible, including this one! Then of course I think the best way to help people overcome imposter syndrome is to ensure our employee base reflects their lived experience, so when they experience HubSpot, they see folx from all backgrounds and are actively excited to apply and grow with us.

Hello Katie Burke, I wanted to know what is your biggest challenge or obstacle having a remote and global workforce from an HR perspective? I think the biggest challenge is making everyone feel connected to each other and to the mission of a company in a way that scales and yet feels personal. Our team is working on it daily, but creating a personal experience while scaling fast is incredibly hard — but so imperative.

This was my only chance to see our Ireland team IRL over the past two years and we made it fun, masks and all!

Does HubSpot hire for industry verticals or only region specific? Considering that if someone has worked with a specific clientele from say a pharma industry would there be roles like that or mostly they are generic/across industries and not industry specific. We typically do not, no — one of the coolest things about HubSpot is we serve a wide variety of businesses looking to grow, so our go to market teams need to be able to speak to a variety of verticals. We do have certain jobs that seek expertise in complexity (as an example, our larger customers often require either technical services or sales engineering that is fairly robust, and our HubSpot for X program does have some specific focus areas in terms of organizations partnering with us, but otherwise, most roles at HubSpot are vertical agnostic as it relates to experience.

Does HubSpot ever consider part-time arrangements for positions? I’m in the midst of a career transition and am really interested in part-time work with a great organization. Right now we offer part time contracting roles but don’t have formal part time postings. It’s something we are considering long-term, keep an eye on our jobs site to learn more!

How is HubSpot different under Yamini’s leadership versus Brian’s? The first thing I always say to this question is that Brian is still our Chairperson and a key decision maker in big strategic questions and priorities for HubSpot. The second is that both Yamini and Brian are fantastic, and that they (alongside Dharmesh) are really aligned about the future of the company and on the things we care about most, so things haven’t changed a ton. Candidly, I’ve really enjoyed working for both of them, so let me share a few things I really like about working with Yamini for folks who may not know her super well well. First, she really knows her stuff. She knows the business cold and when she shows up at a meeting she does so really having done her homework — her business acumen is truly impressive. Second, she really cares about talent and people. Having seen scale before, she knows that recruiting, performance reviews, and leadership development are mission critical to helping us get to the next level, so regardless of which team you’re joining that shines through in her approach. The third is she is super thoughtful — she spends a lot of time listening to people (customers, partners, and employees) and it shows in her approach and feedback. On a lighter note, she’s a great human who is a caring leader, mother, and steward of our business and somehow makes room to do yoga regularly, took up drumming, and knows a ton about wine and classic rock, what’s not to love about that!? TL;DR there are some minor style differences between Brian and Yamini, but they (and Dharmesh plus our leadership team) are very aligned in values and vision, so it doesn’t feel super different, and we are lucky enough to have insight from both Yamini and Brian regularly, so it feels like a double win.

How you at HubSpot help out to ensure that people not only come in from diverse fields but succeed also. Give some examples please. I don’t want to tokenize people without their permission with specific examples just given this will be posted publicly for anyone to see, but I would just say that the People Ops team’s learning and development focus area for next year is professional development to drive equity, so it’s a core element of our work and we are committed not just to hiring diverse teams, but also to helping under-represented groups succeed during their tenure at HubSpot in meaningful ways. A few examples that come to mind for me include our HubSpot Returners Program focused on welcoming folks back to the workforce after career breaks, which has been impactful not just in hiring wonderful people but growing their impact at HubSpot as well. I can think of several female and BIPOC leaders who are managing for the first time at HubSpot thanks to internal career growth, and I can also think of several folks who had never worked in tech prior to coming to HubSpot who are thriving in their roles. A person I really adore at HubSpot completed coursework using HubSpot’s tuition reimbursement, switched teams entirely, completed a program, and just secured an awesome full-time job with a team of people they are really pumped about all within the organization over five years. I just have to say it still warms my heart to see people without formal tech experience prior to HubSpot thrive here.

Katie Burke thank you for opening a post/discussion on HubSpot! Looking at your LinkedIn profile, I see you’re coming up on 9 years with the company, congratulations! I’d love to know what first grabbed your attention and also what has kept you here so many years? I hope you have a wonderful weekend! Thank you so much! What grabbed my attention was the people — my classmate Brad Coffey (now the Chief Customer Officer at HubSpot Ventures investment Pipe) worked here and raved about it. Ultimately, life is short and you want to work with smart, interesting people, so when I was looking for a new role, I called Brad. I loved the idea of inbound marketing, and had used HubSpot a little bit in my previous role, but the idea of building a career in tech just seemed odd to me. I thought I would stay here a year or two, and nine years later, I’m so glad I took the leap and that Brad helped me get connected to HubSpot! What’s kept me here is our people and culture, but also our growth — my first project here was our Dublin office opening. I look now at our 12 entities globally and the incredible growth we’ve seen around the world, and truly can’t believe what we’ve done and what’s ahead of us, so for me it’s people and possibility, then and now.

How is power recognized and navigated in a team? I don’t have a great answer here to be honest, except to say that we are a pretty transparent organization, and that one of our values is humility, so wielding power to try to get things done here doesn’t tend to resonate or work. But I also recognize power is inherent in a lot of relationships and decisions, so I would just say with great power comes great responsibility, and that our management and leadership training really tries to focus on how we support and champion people in meaningful ways. I also think our value of transparency helps a lot here — as an example, one way an organization hoards power is often with employee feedback. The raw comments from our employee survey are shared with the entire organization, so everyone feels like they have a real voice in creating change in the company, regardless of level, tenure, or other variables that often impact power or perceived power.

How open are your recruiters/hiring managers to working with teachers or educators looking to pivot? We are fortunate to have a bunch of folks within our team who have backgrounds in education. My honest answer is that we’d love to have you, and that if you’re making a career switch you may have to do more preparation work than another candidate might, so just know that coming in that we would love to and be honored to have you on our team! Educators have super powers in communication, coaching, and clarity, so I always feel fortunate to have folks with education backgrounds in our org — People Ops, Enablement, Customer Success, and Sales are all organizations I know of off hand with all stars who used to work in education, but I’m sure there are many more!

When you have a lot of different skills, what is the best method for picking a niche? If I were searching for a role right now, I would likely narrow the jobs I was interested in to 3 roles then do a search on LinkedIn for people currently in those roles (or similar ones) for context on their backgrounds and how they might line up (or not) with mine. In parallel, I would watch any short videos on the careers site or on HubSpot Life social accounts to get context on how people actually spend their days, and use that to inform which role would give me the most energy. I always recommend people pick 1–3 key roles total to apply to, any more than that and you’re just going to get frustrated.

What is your stance on remote work? Fully support it! We had 10% of our folks working remotely before the pandemic, and over the pandemic that number has increased significantly. We believe you can do your best work from anywhere we have an entity (details on that in the next question), you can read more about that here.

Can I work from anywhere with HubSpot? Sadly, no. We are a public company and really value compliance, so we offer roles in the entities listed on our website (which currently includes the United States, Canada (Ontario specifically for now), Colombia, Ireland, Germany, France, Belgium, Japan, Australia, Singapore, and the United Kingdom). We offer remote work in all of those locations and continue to add to that list over time, but you cannot currently work at HubSpot full-time from Bali or any other country not on that list. Once employed at HubSpot, we do offer team members temporary mobility to allow work-authorized folx to work from their home country for limited periods of time.

As HubSpot continues to target SMBs and startups, how has the hiring philosophy/strategy shifted? And what do you hope to keep the same? I don’t think our philosophy has changed all that much to be honest. What has changed is our approach — I think our recruiting team has made incredible progress on matching our recruiting approach to align with our DI&B principles but also to align with our hybrid work commitments, helping us find great folks globally, and also using data and technology to inform our processes. I think a few things that are more important than ever are: a growth mindset, a sense of humor and a sense of purpose, a willingness to dig in (we are very much a doing culture, so if you’re someone who just wants to consult…we likely aren’t the spot for you), then I would just say excellence — regardless of whether you join our Product and Engineering team, our Support team, our Sales team, or our Security team, we want folks really seeking excellence in everything they do. Finally, we are a mission driven company, so I really value people who care about the world and the impact they have on it.

Hi Katie! Thanks for posting this. Could you give some tips on how to have a successful first interview? Sure! Most importantly, be yourself. Second, do your homework — for me, I prep a list of my interviewers along with a specific question or two for each of them alongside a list of general questions — researching the questions helps me better refine my responses and answers. Finally, I write down my version of success — what are three things that if I’ve conveyed them would make me proud of how I did even if I don’t get the job? Boiling down your elevator pitch helps you be more concise and specific in the examples you provide on each response.

Love this! What is HubSpot’s approach to remote work and overall greater work life balance for employees? I covered these above, but in short, we are big fans of building your work around your life, not the other way around, and have designed our approach to culture to reflect that commitment. You can read all about the details of our hybrid approach here.

Shakarra on our CSM team: What kinds of questions should a candidate ask a recruiter? Is it okay to ask about things like salary ranges, assessment rubrics etc? I asked Shakarra’s recruiter from our CS team for pro tips here (thank you, Kristen!) and she said: “Customer Success” can really vary at every company so she spends the first few minutes learning about a candidate’s experience and typically has an idea of a strong potential match. She typically asks about what you’re looking for in your next opportunity (including compensation and role expectations) to ensure we don’t get far along in a process with misaligned expectations-that’s a great time for a candidate to be up front about what’s important to them as they consider a change.

With regard to assessments, Kristen’s advice was to read through the prep materials she sends along to candidates — going into a face to face round, you should have links to our blog, consider watching a recent webinar or Q&A session from the team, and clarity on the format of the interviews and what attributes they will be testing on. All of those are good things to ask your recruiter about, and our team is happy to help folks there. In return, Kristen suggests candidates prep questions that are role or team specific versus generic culture questions that are often readily answered in HubSpot’s blog posts or content — you’ll get more relevant answers and build a deeper connection with the interview team.

Will you have some focus on Veterans and Milspouses in your recruiting? We picked our hybrid approach specifically because it allows folks like veterans and military spouses to build careers with us, so the answer is a resounding yes. We do not have a formal separate military recruiting program at this time, but we do have some very proud veterans and military spouses within HubSpot who are wonderful additions to our culture and we’d love to have even more.

Can you please walk me through the screening process at HubSpot done before commencing the selection process? This completely depends on the role and team, but a human being looks through all of the applications in review — I’ve heard people suggest that bots do or that we automate that part of the equation, but nope, it’s assessed by a human being. Typically it’s focused on aligning skills with the job needs and specific guidance from the hiring manager, so we do our best here, hope that helps for context!

What is the most efficient and effective way to learn best practices from HubSpot’s amazing People Org? Join HubSpot? Hire from HubSpot? Katie writes a book? My team really really tries to share our work externally wherever we possibly can, so your best bet is to follow some of my amazing teammates, but I’ve curated a few helpful links that may be useful to people below. Of course, there’s no substitute for joining our team, and our team is hiring, but if that’s not:

-Eimear Marrinan and Meaghan Williams on Remote-Inclusive Cultures

-How to Create a Remote Employer Brand by Hannah Fleishman

-My teammate Mary talking about Return to Work inclusivity on our Culture Happens podcast or my teammates Erica, Jill, and Becca talking about onboarding in a remote world, also on Culture Happens.

-Becky McCullough talking about The Great Rehiring with the team at Hired

-And of course if you’re into Tik Tok, my teammate Viennie has you covered with regular content and my teammate Luke posts regularly from our team in Australia, and our employer brand team continues to do amazing things on our HubSpotLife accounts on both Twitter and Instagram.

-Finally, for aspiring CPOs, I wrote about the best hardest job with a bunch of concrete tips and tricks and of course the Culture Code remains the definitive place to learn all about our culture!

What process does HubSpot implement to assess candidates who may not have tech industry employment history but do have transferable skills, especially for higher level management positions? We start by narrowing the skills and requirements to be true requirements versus “nice to haves” so we really focus on the highest impact attributes for a given role to give candidates of all backgrounds the chance to land a role. We train our recruiters to look for those skills and attributes specifically in screening, and I think many of our recruiters have a real passion for helping career or industry switching folks land roles here as many of them have had similar journeys.

What is the one most important thing to HubSpot when it comes to DEI and making sure all employees are treated equally and fairly? I think it’s pretty telling that our Anti-Racism training is something every single employee and manager in the organization takes. To me, it’s a clear sign when you start at HubSpot that we care about walking the walk, not talking the talk. That doesn’t mean we are perfect, but I like that it sets a high bar for our commitment to inclusion and that it’s part of our business onboarding versus an afterthought. Aside from that, the most important thing is listening — we don’t get everything right, but I think we are good at listening and responding when we are missing the mark.

What is a skill that is needed but underrated? I said it above, but I really do think a sense of humor goes a long way at HubSpot and just in general. If you can laugh easily at yourself, it’s so much easier to laugh off a mistake and learn from it. I take my work seriously, but never take myself too seriously, and I love candidates who do the same. Life is short, as is noted in our Culture Code, I want to work with people who like to have fun.

Do you hire internationally/global diverse talent and remotely? Yes, yes, and yes, but only in the entities where we operate, so be sure to check our job site for current openings. As a public company that cares a lot about compliance, we can’t hire yet in Bali or other locations where we don’t have entities, but the UK and Canada (Ontario specifically) are our two newest additions and we are hiring in both markets.

Are you growing in LatAm/India/other countries? We are growing in LatAm, yes, specifically in Colombia, our team there is over 200 people! The team that serves India currently operates out of Singapore, we’ll be sure to post if that changes at any point.

Missing a few VIPs, but our People Operations Leadership team made it out for one nice dinner in the last three years, it’s the little things in a pandemic!!

I also wanted to ask ‘it feels like the values of HubSpot doesn’t live on a wall, or on a paper but in the everyday actions of everyone in the organization. As you think about 2022, what plans do you have to keep that momentum to keep employees feeling empowered? We really try! On plans for momentum, I would say I’m most excited about where we are heading on ESG — we have a great group of people working on HubSpot’s long term reach and impact, and we are currently hiring to build a dedicated group focused on these issues long-term. I personally believe that the last two years will make it even more imperative that employees don’t just feel good about the job they are doing, but also that the company they work for has a positive impact on diversity, on communities, and on the world around us. So to me, it’s about extending our values not just to our daily work, but to the impact we can have on the world as a result of our growth and culture.

What did HubSpot learn from Global Week of Rest? Honestly, that doing Weeks of Rest are a lot of work:) All kidding aside, it took a ton of work from our Ops and Support teams to ensure that we nailed the execution of the week with limited notice, so one learning for next year was we have to announce it even further in advance to really work. Second learning is to connect your customers and partners to the message — conventional wisdom would suggest that our customers were livid we were taking a break for the week, and the reaction was just the opposite. We connected rest to our ability to serve customer needs long-term, and I think people appreciated that. Finally, the leadership team has to walk the walk — our now CEO Yamini went star gazing (literally) with her family, our General Counsel did a big bike race, and I took a trip with my sister — if leadership is sending emails all week, it defeats the entire point.

How many Boomerang employees does HubSpot have? We have a few, and we are really proud of the folks who have returned to HubSpot. What I will say generally though about boomerangs is that they CAN be wonderful, but you have to treat them with caution. Let’s use a funny example — if I go back to my high school today, it’s been decades since I walked those halls, so I’m going to have a lot of nostalgia about how things used to be. That’s sweet if I’m just visiting, but if I try to relive my high school days and constantly talk about the way things used to be, it’s not going to be fun for my teammates, or ultimately for me long-term. So it’s imperative boomerang employees are excited about where the company is going, not just where it’s been, and that they are energized by the phase of the business you’re currently navigating. With that being said, a former Support rep left for a few years and just rejoined us as a software engineer, and that just warms my heart, so glad to have her back!

How does one person learn all of HubSpot? Our product grows in breadth and functionality by the day, so it’s really hard to keep up with *everything* but I think the end result is still that our customers get a product that is easy, powerful, and feel our commitment to constantly innovating. I think a cool thing our Voice of the Customer and Product teams have worked together on with marketing is more in-app messaging and cues to help direct people to new functionality or features, so that helps, as does HubSpot Academy, so those are the best places to start. For folks trying to learn more about our culture, the Culture Happens podcast is a great resource, as is our Careers Blog.

What makes HubSpot a Best Place to Work? A lot of people asked about our strategy for Glassdoor or Comparably, and our employer brand team is indeed amazing. But the driving force behind your culture has to be what you deliver for your employees every day, so instead of focusing on how to “spin” your culture to appeal to candidates, spend time thinking about what makes your culture truly unique, then lean into making that experience a reality day to day. For us in particular, I would say transparency and autonomy are key drivers of our culture, as is the degree to which we use our values to drive everything we do as an organization. In addition, the seriousness with which we treat and address employee feedback I think has always been one of the ways in which we differentiate ourselves from other organizations. At the end of the day, our people make the place and always have.

I hope this is helpful to folks considering life at HubSpot — in a crowded talent market, ensure candidates have access to helpful context on our culture is imperative, so let me know what I missed. We hope you’ll join our team, thanks for your thoughtful questions, feedback, and applications!

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Katie Burke

Chief People Officer at HubSpot. Proud graduate of Bates College, MIT Sloan, and Space Camp. On the interwebs @katieburkie