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Stella Garber is VP of Marketing at Trello. Previously, Stella was CEO and cofounder of matchist, a matching marketplace for developers and entrepreneurs which was acquired in 2015 after winning the New Venture Challenge at the University of Chicago. Before that, Stella was on the founding team of venture backed payments startup FeeFighters, acquired by Groupon in 2015.

A frequent contributor and speaker, she has spoken on topics related to entrepreneurship and marketing at Web Summit, Inbound, Collision, Forbes, and The Family. She is also a mentor at TechStars Chicago. 

She holds an MBA from The University of Chicago Booth School of Business where she was a Herman Fellow.

You can follow her on Twitter: @startupstella

She will be live on Dec 15, starting at 930 AM PT for one and a half hours during which she will answer as many questions as possible.

  • HQ

    Hila Qu

    4 months ago #

    Hey Stella,

    Super cool to have you on GH!

    1) I read from your Linkedin you were the first marketing hire at Trello, and have helped grow the user base from 4M to 17M. That's very impressive. What do you think is the most challenging aspect of growing Trello? Which aspect of marketing Trello do you have most fun with?

    2) You have an impressive background, as a founder & marketing leader, what's your secrete to have tried so many things and found success in many of them?

    3) There are many project management tools, paid, free, specialized. With so many players, what do you think of the future of Trello will be like? Used by everyone in the planet:)?

    Look forward to hear your thoughts:)

    Hila

    • SG

      Stella Garber

      3 months ago #

      2) Great question! I’ve found that with every opportunity that comes along, it’s important to have a framework for what’s important to you in order to make optimal decisions. For example, I’ve noticed the things that attract me are really smart people, who have the same values, solving a problem that I’m passionate about.

      That might seem general - but for the first one, I always want to feel like I’m the dumbest person in the room. If that’s not the case, the team is probably not the best fit for what I’m looking for. Values are also super important because when you make career decisions, you have tp optimize for the long term, and nothing helps you understand how people will operate in tough situations more than knowing their values (making sure they align with your own). And for the third question, I have to LOVE and be able to identify the problem/product. I was a HUGE Trello user before joining the company- I was using Trello to run my startup and plan my wedding, so I was impressed with the product and understood the power of using one tool to manage many aspects of life.

    • SG

      Stella Garber

      3 months ago #

      Hi Hila! It’s great to be here! Now for your questions:

      1) The most challenging aspect of growing Trello is also the thing that’s the most fun: Trello can be used for just about any project- its horizontal nature means everyone from Fortune 500 companies to book clubs use it to organize their teams. As a marketer, this means we have to be able to appeal to literally all kinds of users. Our user privacy philosophy is also very stringent, so we have 0 access to user generated content (rightly so!) which means that marketing doesn’t have organic ways of knowing how to target/segment users by their use case. Again- fun because we’re not restricted to a certain vertical, but challenging because we have to be able to relate to users without knowing their intent.

    • SG

      Stella Garber

      3 months ago #

      3) I hope so! The thing that really differentiates Trello is ease of use- my mom, who is not a super tech savvy individual, uses Trello to share recipes with her friends. I can’t imagine this being the case for any other tool that I'm using in my tech first lifestyle. The ease of use opens Trello up to literally the whole world- primarily in business collaboration because that’s when humans are staring at screens the longest, but also outside of work. Trello allows people to be themselves and use one framework to empower teams in all parts of life.

      Thanks again for your great questions Hila!

  • DH

    David Hobson

    3 months ago #

    YES! Awesome to have you here - thank you for your time.

    [QUESTION ON GROWTH]
    Can you think of one, single event that drove an unusually high amount of sign-ups to Trello? Either intentional or unintentional. If so, would love to hear more. Keep doing amazing things, we use Trello everyday!

    Congrats on the success and thanks for your time :-)

    • SG

      Stella Garber

      3 months ago #

      Hi David- When I initially joined Trello, I wanted to show the (small) team the benefits of a good PR strategy. We were about to surpass 5 million users, so our first big marketing campaign utilized our momentum to delight (sharing stats about Trello in a fun infographic) but also draw signups by giving an exclusive to a popular tech publication. Trello hadn’t been in the press much before then, so the exposure created a rush of signups that was undeniable and changed the trajectory of our user signup growth for that quarter. Of course- PR doesn’t work like this every time, but it was a big win for us.

      • DH

        David Hobson

        3 months ago #

        Thanks Stella! Congratulations and appreciate you answering this, love these kinds of insights. Keep up the amazing work and we appreciate you for taking the time. Very encouraging.

  • AA

    Aldin A

    3 months ago #

    Hey Stella,

    Great to have you here.

    1)Building out matchist what did you learn about scaling a marketplace? What challenges did you encounter and how did you solve them?

    2)What are the most important lessons you've learned in your career about building successful marketplaces?

    3)How do you retain your users, if your user only need to use your app occasionally by nature (ex matchist)?
    If your app isn't used frequently building up the habit is hard, which makes it even harder to retain the user.
    How do you go about trying to stay top of mind so when the user has a need that your app solves they think of you?

    Excited to learn from you,
    Aldin

    • SG

      Stella Garber

      3 months ago #

      2) If I were to start another company, it would absolutely not be a marketplace! One thing I’ve learned is that if a business you think should exist doesn’t…that means others have tried it and for some reason it didn’t work out, not that the lack of competition is the validation you're looking for to start the business.

    • SG

      Stella Garber

      3 months ago #

      Hi Aldin - It’s great to be here!

      1) Marketplaces are really, really hard! Like really, hard. The economics look great when you’re modeling them, but the cost and hustle to get those economics at scale is extremely difficult. That’s why so many marketplaces are either shut down, or a few break off and become wildly successful due to network effects. Our initial thoughts were to scale the supply side then focus on demand, but we had a much easier time with supply and should’ve spent much more time thinking on demand. We solved these issues by tweaking our demand gen model, but never got to a point where we figured out customer acquisition on the demand side to the point of scale (before acquisition).

    • SG

      Stella Garber

      3 months ago #

      3) Great question. For us, it had to do with understanding the supply side of our marketplace. For freelance developers, getting paid on time was the #2 concern after finding good projects. We hypothesized that they would continue to use our payment portal simply to make sure they got paid on time - and we were right. In some cases, the client “bought out” rights to work with the devs offline, which was totally fine by us. But the devs almost never took the work offline for fear of being cut off from the network or screwed by clients who didn’t pay.

  • AA

    Adriano Almeida

    3 months ago #

    Hi Stella, great having you here.

    One question that always comes to my mind is how to upsell a product when you already have an awesome freemium? From my point of view, Trello's free option already generates an infinity of value and is a very complete solution, so how can the marketing team work to create that necessity on the customers (business and no-business) so they'd be willing to pay for the Business Class or Enterprise plans? What actions do you take to generate this upsell?

    Cheers

    • SG

      Stella Garber

      3 months ago #

      Hi Adriano - For Trello, we wanted to give away as much as possible in the free product in order to spur growth. Our initial paid features focused on admin features like user management and security - the end user doesn’t benefit much, but the company’s IT department sure cares! In the last couple of years, we’ve shifted our focus to making the paid product more useful for the end user by building out our platform.

      We see Trello as a blank slate where, say marketing professionals, can customize their workflows by using the Dropbox, SurveyMonkey, Mailchimp, Twitter or any other handful of Power-Ups. Having data all connected and in one place just makes everyone’s lives easier and is a boon for teams. Trello is the platform where your team can make its own unique workflow using all the Power-Ups you want…we see this flexibility and customization as the future of workplace collaboration…so our paid product features will support those goals.

  • RB

    Ry B

    3 months ago #

    Hi Stella

    Thanks for doing this!

    1)How do you look at hiring? Can you talk about some of the mistakes you've made hiring (and also seen others make)? What have you learned about hiring A+ talents?

    2)What are traits a manager needs to bring out the best in their employees?How did you go about empowering employees at matchist and trello?

    3)How do you look at competition, specifically when you're going up against bigger, and better-funded competitors? How does that affect your strategic plan, if it does at all? What is your mindset when you go to compete against the 800-pound gorillas in your space?

    Thanks

    • SG

      Stella Garber

      3 months ago #

      Hi Ry!

      1) Hiring is like dating- it has to make sense for both parties. There may be a lot of potential candidates out there, but there is going to be one that is the best fit for the relationship. Cheesy I know, but also true. Hiring also depends on the stage of the startup- in the beginning, you want to look for generalists who are smart, adaptable and have a broad skillset. As the company and your team grows, you start looking for people with much more specialized skillsets. The good news is that generalists tend to be drawn to smaller companies that need their flexibility, and specialists (imho!) like the stability of larger companies.

      The thing I’ve learned is that the best way to gauge a person’s potential success at a job is to have them interview doing a project or work that they would actually be doing, and have them interact with many people on that team about the specific project (rather than just a get to know you interview).

    • SG

      Stella Garber

      3 months ago #

      2) A manager needs to set clear expectations, and provide an environment where people can succeed. Trello has this great philosophy of “hire smart people, and let them get shit done.” I’m a huge believer in doing just that- when you have great people, your job as a manager is to clear the way so they can do their job. You also have to have empathy and develop a relationship with people on a personal level. A lot of research has shown that the more open people feel to be themselves at work, the more happy and productive they are. I’m always trying to think of better ways to be a manager and soliciting feedback to make team processes better.

    • SG

      Stella Garber

      3 months ago #

      3) There is the tendency to look at big competitors and think they have all the answers because of their vast resources. However, big companies have their own host of challenges- politics, bureaucracy, and a slower pace. Startups often have competitive advantage in their ability to move quickly, try a lot of different things, and take bigger risks. That being said, it’s hard not to pay attention to the 800-pound gorilla. In my career, it’s served me well to have a hypothesis on strategy that’s well researched, and testing all the way without spending too much time paying attention to what others are doing.

  • DH

    Dani Hart

    3 months ago #

    Hi Stella,

    So awesome to have you here today! I'm curious...

    1. How is the internal team at Trello structured for growth? Are there different departments that come together to work on AARRR efforts?
    2. How are objectives set for your team? Is there a specific timeframe that you measure your efforts?
    3. What tools are in your marketing/growth stack?

    Looking forward to learning from your response.

    Cheers,
    Dani

  • SA

    Shaker A

    3 months ago #

    Hi Stella

    Thanks for being here!

    1)How did you initially source and get the supply side on to the network when matchist was started, and didn't yet have the
    demand necessary to naturally attract the supply side? How did you build credibility with them and get them to give you
    a shot?

    2)Matching developers with the right skills to the entrepreneurs that need those skills can get complicated as you get bigger (I imagine). What did you do at matchist to help make the matching process easier and better for both parties?

    Thanks

    • SG

      Stella Garber

      3 months ago #

      Hi Shaker-

      1) The supply side ended up being way easier than we expected. We made it dead simple for developers to sign up and see value in our product - they had no risk or downside and would only pay us if they were able to get work through matchist. In the first week of launch, we attracted >300 devs which was amazing and allowed us to be hyper selective for who we wanted on the platform. Just like any early stage startup, the beginning is all about hustle and relationships, so the first active developers all developed relationships with us (the founders) and a foundation of trust. This is obviously not scalable, but is very important when testing the proof of concept.

    • SG

      Stella Garber

      3 months ago #

      2) Initially, we wanted to automate the matching process as much as possible. We developed an algorithm with inputs and outputs to perform matches but what we quickly realized was that it was impossible to provide the level of service we wanted without some human interaction. Partly, a human was able to vet entrepreneurs for how serious they were or their access to actual funds before matching them with developers. A human also developed a relationship with both parties and fostered trust in the process.

  • SG

    Stella Garber

    3 months ago #

    Hi John -

    1) Consistently word-of-mouth surprises me with how powerful it as a source of new uses.
    2) We're figuring that out now.
    3) No- but we think Trello is most powerful when used in teams.
    4) Oh gosh. There are so many! I love the example of using Trello for community engagement - some cities have a Trello board where people can submit requests or get information, and they use the voting feature to look at what issues should get attention.

  • GM

    George Mills

    4 months ago #

    Let's say i invented slack. I am offering same features as Skype. Why would people use my service?

    • SG

      Stella Garber

      3 months ago #

      Hi George - Early adopters are always looking for the Next Big Thing. They will try just about anything and recommend it to their friends if they like it. Skype has a lot of issues, so Slack’s friendly user experience, approachable brand, and easy to use product explain why so many people love it (and why user adoption has grown so quickly!).

  • SM

    saji miri

    4 months ago #

    Hi
    I am from Iran and most of the products that we work on here are somehow a clone of successful global products but with some features focused on our local user needs.
    I want to know what is the right approach for us in marketing considering these famous global alternatives that are available (Note: some of these products are not accessible in here officialy but can be accessed using vpn etc)?
    Thanks!

  • SK

    Sil Kreulen

    3 months ago #

    Hi Stella. Great to have you here.

    A wise growth guru once whispered in my ear: ''If information was the key, we would all have a unicorn start-up. It's not about what you know, but with you do with the data and information you have.''

    With that being said:
    - What's your perspective on maximizing the learning curve within a growth (marketing) team?

    - What's the single piece of advice that you would give to execute fast as a growth marketer/team?

    - If a researcher aims to dive deeper into the topic growth hacking/marketing, which specific area would you advice him to focus on? Insights in which topics could help the growth of your company?

    Thanks,

    Sil

    • SG

      Stella Garber

      3 months ago #

      Hi Sil-

      1) Communication! Especially as a marketing team grows, it becomes more important to establish a culture of sharing what everyone is learning as they’re doing projects, whether it relates to data, content, social, etc. It’s also important to establish a culture where it’s ok to fail. At our weekly marketing team meeting, we go around and say one thing that we failed at this week (we used to call it Fuck Up Fridays when our meetings were on Friday!). This makes it ok to fail- which is an important part of learning and growth.

      • AA

        Anuj Adhiya

        3 months ago #

        I wish I could upvote this response a few more times.
        IMO if anyone takes anything away from this AMA - it would be to internalize this.

    • SG

      Stella Garber

      3 months ago #

      3) Customer acquisition! Not enough companies put appropriate resources into understanding where customers are coming from, why they signup/buy, and why they stick around.

    • SG

      Stella Garber

      3 months ago #

      2) Be dynamic and goal oriented. It’s important to know why you’re doing something and what you hope to get out of it…that might seem obvious, but the end goal can sometimes get lost as people work on projects. So writing down the goal, then being dynamic about changing directions and not sticking to a plan when better ideas come up will help your team execute faster, and more strategically.

  • PK

    Prateek Keshari

    3 months ago #

    Hi Stella! Great to have you here.

    1) What's the strategy you follow to channel content on Social Media? What's the process to understand what type of content your audience will resonate with?
    2) What's your top priority in 2017 as a marketing leader and why?

    Look forward to hear your thoughts! :)

    • SG

      Stella Garber

      3 months ago #

      Hi Prateek-
      1) Our Content and Community team have a healthy feedback loop where we are always sharing what content is working on a channel by channel basis. This informs both our Content strategy (what should we be writing about?) as well as our social strategy (where is our audience? What do they want to hear from us?).

    • SG

      Stella Garber

      3 months ago #

      2) Top priority for 2017…oy! Our team is growing really fast, so the thing I’m thinking about right now is onboarding and making sure each new hire has as great of an onboarding experience as people did when they joined a smaller team. Our team’s culture and ability to execute depend on new hires successfully and quickly integrating into the team, understanding team and company priorities, and where/how they fit in.

  • PB

    Plamen Barzev

    3 months ago #

    Hey Stella,

    So glad to have you here! I'm a huge fan of Trello and in our company we use it for almost everything. Thus said, I must admit that we pay for Trello Gold mostly as a donation, because we believe in supporting cool services.

    My question:

    - Trello's integrations with the likes of Zapier, IFTTT, Punchtime, etc are great and make the platform even more useful. Could you reveal what are your relationships with these third-parties? Are monetizing these integrations or you are just doing it because it makes the overall product better?

    Thank you!

    • SG

      Stella Garber

      3 months ago #

      Hi Plamen -

      It depends on the Power-Up! Some developers make the Power-Up because it’s just awesome to have and makes their service more powerful to users, and some monetize from it. For the most part, it’s the former.

  • AT

    Amit Thacker

    3 months ago #

    Hi Stella,

    Thanks for taking the time to share your insights.

    What were your early growth challenges at Trello; how did you plan the strategy. Where did you go for data, given that it were early days and user behaviour/ target group data would have been very limited. I ask this because I remember Trello addressing agile/scrum type users almost exclusively in the early days and then it seemed like someone internally may have had a marketing 'eureka' moment and said hey let us address anyone who wants to record thing as a todo.

    • SG

      Stella Garber

      3 months ago #

      Hi Amit- Actually, the product was built to be totally horizontal from day one. Since there was no formal marketing or growth function for the first couple of years, growth was all word of mouth. Since Trello was initially developed by Fog Creek Software and Joel Spolsky had an amazing existing audience, the initial userbase tended to be more technical. The product team specifically didn't integrate a lot of features more technical users were asking for because they would've made the product less horizontal.

  • AA

    Anuj Adhiya

    3 months ago #

    Hey Stella - stoked to have you on!

    Common advice given to startup founders is to "niche down" and develop your v1.0 with the ideal user persona in mind.
    To me, Trello is the antithesis of that advice. It's a "horizontal" product who's list-making use cases are limited only by imagination and creativity.

    If that characterization is correct, then what advice would you have for folks developing products that share that horizontal aspect of Trello in terms of:
    a. how to go about customer development
    b. determining product/market fit
    c. picking the right marketing strategy

    • SG

      Stella Garber

      3 months ago #

      Hi Anuj- You have to have a lot of patience and capital to build a product that is truly horizontal. Trello did not monetize for its first few years in existence with the goal of growing our userbase before focusing on monetization....that is not a luxury most startups have. In this case, our unique ability to do this centered on Trello being a product of Fog Creek Software, where revenue was derived from other tools. So the advice I'd give founders is unless you do have those luxuries, don't do it! Be explicit in learning about your vertical and understanding your customer. I realize this is the opposite strategy for Trello, but that was partly why I joined the company - to learn about a super non-traditional, but successful startup.

  • AS

    Adam Szabo

    3 months ago #

    Hi Stella,

    Trello is one of my favorite SaaS I couldn't live without!

    If you were to hire a new marketer in your team, what qualifications, skills or experience would you love to see on their CV?

    • SG

      Stella Garber

      3 months ago #

      Hi Adam- That's amazing to hear! As our marketing team grows, we're looking for people with more specialized skillsets. For example, we are hiring an Email Marketing Manager right now, and for this hire, we're looking for someone with deep experience working with ESPs and building out an email program.

  • AC

    Aalim Chin

    3 months ago #

    Hi Stella.
    What's your best strategy for keeping motivated to focus on your work?

  • BG

    Brooks Golden

    3 months ago #

    Hey Stella, how are you!

    We're working on an employer branding diagnostic tool for our clients and would love some insight from Trello. How does your marketing team impact candidate perception of the company (vs. HR or senior management)?

  • MB

    Marco Burgin

    3 months ago #

    Hey Stella! ;)

    My question is How Trello grow from 0 to 1000 users without little marketing budget.

    What was the best strategy?

    Thanks a lot

  • SG

    Stella Garber

    3 months ago #

    That's all the time I have today folks! See you on twitter- I'm @startupstella

  • JM

    Jason Meresman

    3 months ago #

    Hi Stella,

    Thanks for the AMA!

    My undestanding is that Trello mandated that the product work across desktop and mobile from day one.

    - Are mobile users the majority or minority of your users?

    - Do you see any difference in engagement between mobile users vs. desktop users?

    - And finally, is there any difference in the likelihood of going premium for mobile users vs. desktop users?

    Jason

  • JP

    John Phamvan

    3 months ago #

    Hi Stella!

    Thanks for doing this!

    1. What was the most surprising source of new users for you?
    2. How do you know a customer is ready to go from free to a paid Trello user?
    3. Do you internally treat single users customers different from organizations when it comes to growth and marketing? In what ways?
    4. More fun, what is the niftiest way you've seen someone use Trello that the team never thought of?

    Thanks,
    John

  • SV

    Steve Valencia

    3 months ago #

    Hi Stella-- Thanks for the AMA! Not sure if this will make it to you in time... but wondering how you go about marketing to large orgs/enterprise accounts vs. the individual end user? For trello has it been typically an upsell/land&expand strategy, or do you guys also dedicated time going after larger accounts from the get-go?

    Thanks again!
    Steve

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