Here's How We're Leveling Up HelloSign

Improving HelloSign

This is the year we’re leveling up as a company. We’ve been hustling for a long time and we decided it was time to scale. We held out until the indicators were there and they told us it was time to step on the gas: the metrics were in alignment, the eSignature market was hitting an inflection point in growth and people love both the end user product and our eSignature API.

This last year has seen a lot of change at HelloSign. We’ve grown to twenty-six people, brought on incredibly experienced team members and we’re working on building strong foundations for every aspect of the business.

We’ve always prided ourselves on being an “unsexy” start-up because we have a different philosophy when it comes to company building. For example, we’ve never announced funding, we had a plain website and we generally kept off the radar for a long time. For the first time, we’ve listed our investors on AngelList and our About Us page. 

We’re big believers that fundraising isn’t a metric of success in and of itself – and by announcing fundraising we’d be focusing on the wrong indicator. Instead, we measure success not by the amount of money we raise but by having people use and love our product, end user and API included. 

We have this nice looking new blog, a new office and we just rebranded, so I wanted to share the foundations we’re building this year. 

1. Team 

We stayed lean for a long time, but no more. We’ve grown from 11 people to 26 people so far this year. We’re looking to double again in the next year. 

One key thing we had to do is shift everyone from being a generalist to a specialist and we’ve brought on people with tons of experience to own and grow departments. We’ve also learned a lot about what’s important in a team, versus what isn’t important. I’ll write more about this in the future.

2. Revenue 

Revenue now fully supports our operations and growth — our customers are our investors and it’s an incredible feeling. We work hard to make them the best possible product and they invest in us by subscribing and spreading the word. We’re investing all revenue back into making the product incredible. 

3. Laser focus on the right users 

I'm not a believer in trying to be everything to everyone. We have a lot of inbound signups and they come from all different industries and company sizes. They use HelloSign for dozens of use cases. But we’ve become very judicious about the type of user we’re seeking (versus coming to us) and it’s had a hugely positive impact on our business. 

This is one area I’ll leave a little ambiguous. I can’t reveal all our secrets. But I can just say, doing user analysis is the most valuable thing we’ve done. 

4. Office 

Although an office isn’t an indicator of success, this new office definitely feels good. This is probably the nicest place we’ve worked, especially in the context of where we’ve worked before. We started in coffee shops, moved to cofounder Neal’s living room, upgraded to a converted house in the Haight, moved to a scrappy office in SOMA and now work in an incredible office down the street from Twitter and Uber. 

It may seem trivial, but you can feel the difference when you walk around the new office and see our company branding everywhere. We’re aligning on our identity across the company, from our logo, the website, and the product itself to where we work.


5. Design and brand

We’ve always focused on UX and usability. But in iterating fast and focusing on functionality, sometimes quality design got lost in the mix. We got amazing feedback from our users, but our outward appearance and brand didn’t match the internal passion and energy of what we were doing. We knew we were creating the best eSignature experience available and our brand didn't always reflect that. It was time to revisit this. 

We completely rebranded our site. It’s hard to put a finger on it, but the new brand feels like a closer representation of who we are as a company. (Read a review of our rebrand or check out the post announcing it). 

It’s had an impact on our speed of development. We re-engineered the site using new technology to be faster and more responsive to mobile devices. We’ve been able to quickly spin up and deploy marketing pages for campaigns – something that in the past took a lot of time, custom development work and design.

6. Marketing 

We’ve done some launch marketing in the past, but I think it’s the marketing in-between launches that’s a true indicator of a marketing department. Turns out, most companies do marketing to grow! Due to time constraints, we just haven’t done much of it in the past. We’re now making a big investment in growing the marketing department and putting forth a sustained effort. If we got to our current point without one, I’m hugely optimistic about what we can do with one. 

I’ve learned a lot about marketing in the last six months. There’s a difference between doing general startup marketing that can move the needle on a small user-base and building a marketing organization, which can move the needle on a larger user-base. We’re now making strides to do the latter. 

7. Product

I used to run product, until I talked to one of our investors, who gave some good advice. He said that if the CEO runs a department, that department will get short changed. It’s not intuitive, but each department needs a full owner and advocate. The CEO would inherently make tradeoffs, whereas an owner would continue to make a case for the department. 

Handing over product was one of the hardest things I did, but we realized that with a full development team, it wouldn’t get the attention it needed with me owning it. Based on the improvements we’ve seen since, it was definitely the right decision. 

8. Sales 

I think a lot of startups have visions of becoming the next Dropbox, where everything is self-serve, automated and somehow you end up with a multi-billion dollar company. I think the reality is that most businesses run on sales and we were leaving a lot of money on the table without a sales team. 

We’ve never done sales. We’ve gotten far without it, but I think we haven’t optimized for our audience, which is now going to change. 

9. Business Development 

In the past, we simply weren’t able to chase down high potential BD opportunities, because they’d take months to work out and I didn’t have the bandwidth to do it. I just focused on the biggest ones. Here’s a talk I gave at the 500Startups Unsexy conference about business development. 

We finally have someone committed to going after partnership opportunities and we have some amazing partnerships coming up. 

10. Values 

Values are crucial. I’m not talking about the value posters you see when walking around hospitals, banks or corporate lobbies. I’m talking about the values that actually mean something because people live them every day. When you have a value as a company and believe it in, that value will become part of every decision that everyone makes all the time. 

When you build a feature, should you build something that’s a great user experience or not? Everyone in our company has the same answer to that question, since we value ‘making our users awesome’. It’s not sufficient to build an okay experience - we want something people get so excited about, they’ll mention it over dinner conversations. Kathy Sierra’s video inspires us. 

We’re solidifying our values this year and it’s something we take very seriously.   

What's next?  

This is a big year for us. We certainly still have a lot of things to figure out. But, we’re building foundations for the company and leveling up every aspect of the business. This will set us up to accelerate even more in 2015. Thanks for the support over the years on this journey and supporting our product development. We have a lot more in store including amazing updates to our HelloSign API! 

If you want to get hands on experience with how our API works (and get a feel for features like embedded templates, embedded signing, and embedded requesting), schedule a demo and we'll happily walk you through it.

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