BDC Interview with SpeakUp CEO, Ray Gillenwater


The aha moment for me was two years ago. I was 27 and a Managing Director at BlackBerry at the time, recently promoted to manage Australia and New Zealand. As an employee climbing the ranks, and a student of Communications, I always wondered how execs included their teams in problem solving, ideation, and the decision making process. What I discovered, was pretty surprising.

No one I met had a very good approach. Don’t get me wrong, many tried. I did. I had offsites, strategy sessions, interviews with the teams, and of course we had email chains (blech). Nothing was good enough. I was a busy guy and my team was busy. There was simply no way the manual process of bubbling up ideas and problems to me (the age old method of politicking and/or being the loudest) was going to cut it in the culture I envisioned. I searched for methods, software, and anything that could assist us. I talked to smart people at Korn Ferry, McKinsey, Apple, Google, Gallup – it wasn’t just me, they recognized the same communication gap.

Leaders are flying blind. Employees are at half-throttle, fully aware of the fact their great thinking more than likely won’t result in tangible company change.

Pretty unbelievable until you think about it in the context of how outdated some business practices are and how terrible enterprise software is.

I had just started working with Keith Barney on another project and his customer focus and ability to create amazing user experiences blew me away. I knew that if we found a really cool idea to work on, we would make great partners. The idea for SpeakUp instantly struck him. The passion and effort he puts into his work goes far beyond anyone I’ve ever worked with. And his level of engagement was never fully utilized by the decision makers at his past companies – they just weren’t tapping into his skills and talent in the way that they could have been. He related to the problem SpeakUp solves from the perspective of an employee, and he began working on mockups after our first email exchange.

At the time I was involved in a few software projects, investing, and advising other tech start-ups so it was perfect timing to put everything I learned to use on SpeakUp. We partnered with brilliant engineers. We mapped out features and use-cases. We were ultra disciplined in keeping the early version of the product focused on the most crucial features and we were determined to make the experience end-user focused – something I think too many B2B software companies forget about. After some of the cliche startup drama (which I won’t get into now), half a year, and about $275k of my own savings, we were live with our first customers. Big sigh of relief – they loved it, and we are now past the first point of validation.

We are experimenting every day with different use cases. We even joke that SpeakUp would be perfect in a relationship – “let’s define the problem and then agree on the best solution.” Jokes aside, we are working with a really diverse set of beta customers:

  • We’re helping a global communications company figure out their next big product offering to turnaround slumping growth (and they think they’ve found it, thanks to the team collaborating in SpeakUp)
  • We’re testing to see how useful SpeakUp is to make decisions in software development. Top voted problems become bugs in Bugherd (for example), and then top voted ideas become future features in, let’s say, Trello.
  • SpeakUp is being used to plan a big tech event. Really busy important people with limited time for meetings, and less time for emails, getting together asynchronously in SpeakUp to raise problems/solutions and ideas that result in concrete decisions.

We’ve deployed at an incubator where investors will be able to constructively flag problems and share their ideas. We’re in talks with the NAACP to help their executive committee make decisions without being in the same room. And that’s just a start – we have some of the biggest companies in the world in our pipeline. First things first though, we need to get the product/market fit right, and then experiment with growth strategies until we find the right one for us.

Regardless of the use case, the one thing that puts a smile on my face every single time is when a company exec sends me a note, so excited about all this new stuff they learned about their own company – it’s awesome.

The feeling is the same when we get messages from users talking about how much time they’re saving now that they’re using SpeakUp to replace meetings and the feeling they get when they can see their ideas grow into tangible company progress. That is what gives me and Keith endless energy and passion for this company.

What excites me is transitioning into the age of knowledge workers, as manual jobs, tasks, and operations are replaced by hardware and software. This means that more employees will be paid for their brainpower, and companies that figure out how to extract the best thinking from their teams, will have a competitive advantage. How great is that? Hire amazing people, and figure out how to let them do their best work and you accel past your competitors.

The best side effect of workers being emphasized and respected is the resulting disintegration of command and control power structures at work. Really smart companies have already figured out that running a company like a 14th century monarchy is not the most efficient way to manage a business.

The really cool stuff happens when a company is run more collaboratively, and people start to give a shit, which results in getting more/better work done.

I hope (and will use SpeakUp as a model) that this results in more emphasis placed on workers, everyone in the company sharing in financial success, and a resulting smaller pay gap between execs and employees. Will this help society? Since every company will be a tech company to some extent in the future, then perhaps it will result in better income parity and happier workers.

What do I fear? Relative to SpeakUp, I fear that there are highly paid executives out there that think they have all of the answers and will continue to make decisions without enough information – when there is a goldmine of untapped knowledge within their own organizations. That’s okay, we’re going to focus on decision makers that are already seeking out more insight from their teams, but are just looking for a better way. The dinosaurs will eventually become extinct.

HR gets picked on because so many HR pros operate like it’s 1995. And they deserve it. Fortunately, I see two important changes happening simultaneously:

1) Transitioning from the “HR is a department” or “HR is red tape” mindset to a “HR is the business” or a “people are the most important part of the company” mindset. Love it. When the business has conflict with the HR department, it’s an early indicator of big problems. So I’m glad to see more execs prioritizing HR.

2) New tools and automation. There is a software as a service for almost everything. My friend’s at Hirevue and iGrads can help you do recruiting without flights or hotels. Zenpayroll makes something as complicated and frustrating as paying employees super easy. Workday does…basically everything (full disclosure, one of their partners is a SpeakUp beta user).

HR is an old, boring industry, and it’s (thankfully) being disrupted. There will be plenty more billion dollar startups that come out of optimizing and automating outdated HR processes. And there will be more HR execs looking for work (or retiring) that still think people are easily replaceable cogs in a wheel.

SpeakUp is working on making our awesome beta customers (we love you) as happy as possible. We are learning from this process and working towards product/market fit – that is, figuring out exactly what features to offer to a very specific group of people.

We’ve been in closed beta for about six weeks now, and we are really happy with the quality, speed and utility of the product. Just last week, we sent out our second batch of beta invites and we are refining the onboarding process. We want signing up for SpeakUp to be so simple and obvious that it’s almost like a SpeakUp deployment happens automatically.

On the business side, I’m just now collecting checks from our first round of external investment. We’re planning to exit the beta stage soon and figuring out the PR and marketing that will go along with it. We’ll soon be looking to bring on a technical lead and additional sales and support staff as well.

In terms of features, we will soon be releasing “groups” which will enable us to scale up the size of customer deployments significantly. Customers will be able to create groups to match their internal team structure, matrix teams, and project teams. The next big question we will be looking to answer is: what happens to solutions and ideas after they’re approved? We have some thoughts on how to make post-decision workstreams visible to everyone, so the whole team knows the progress of a decision at any time. Our mobile app is now in development as well – all coming very soon.

Other than that you can expect tons of passion and enthusiasm from us – there is nothing we’d rather be doing. And that’s not a cliche, we literally went down the list of possibilities before we decided to start SpeakUp – and SpeakUp topped the list.

Thanks for the interview and best of luck with BDC! (original post)

Ray Gillenwater