Hi Brandon, nice to meet you. Can you introduce yourself to our readers?

My name is Brandon Mensinga. I’m COO for Trint; I’ve been here for six months. I’m a specialist joining companies at the Series A stage to work with the Founder to professionalise the business. I work to ensure that by the time we finish the Series A we have the right metrics needed to set the company on the right path.

What inspired you to join Trint? Especially after coming over from Signal, a successful Series B company.

When I was finishing up at Signal, I was at that point where I had a good number of venture capital people who I knew in the SaaS industry.

Through that initial entry point and contacts that I had, they referred me back to a wider network of companies all focussed on B2B SaaS. It was wonderful to have an opportunity to look at their portfolios to identify a fit with my particular skill set.

Throughout that process, I had numerous conversations with VCs leading to 20 – 25 actual Founder conversations with Series A companies across London. It was eye-opening in terms of the amount of investment going into companies that are doing fascinating things.

It was great to see what the investments looked like, what the company needed to look like and what the Founder was like. Off the back of those conversations, I came to the realisation that Trint was best positioned for a growth path that aligned with what I wanted to do.

How so?

In order to professionalise the business from Series A to Series B, you need to have the right attributes in the company to ensure that Series B investors would look at it and say, “That’s the right kind of investment to make from a B2B SaaS perspective.”

Trint as a company was attractive for several reasons:

1) Jeff Kofman, the Founder of the business, has a wonderful backstory: he was a war correspondent and foreign correspondent for over 30 years on ABC, CBS and CBC News. He was the person in the field who would report on what was happening in Libya, Iraq, and that sort of thing.

Jeff experienced the pain point of transcription himself. After he interviewed someone, he’d have to transcribe the interview and then get quotes back to HQ for the evening press to be part of that news cycle.

Off the back of those experiences, he founded the company with a couple of developers and quickly built the first version of the product. It was put online and, very quickly, there was huge traction, specifically for journalists with this pain point, as it makes their lives easier.

Jeff is a very charismatic Founder of the business and is really galvanising for the company in terms of our mission. He’s wonderful in front of investors and strategic customers.

As a Founder, he was highly attractive for me to work with and I felt we had a good pairing – he’s the charismatic Founder and I’m the operational right-hand person to help grow the business to a bigger level.

2) It’s the product itself. There was clear and enormous traction for the product as evidenced by a passionate community of journalists, multimedia producers, video producers and editors who simply love the software. It’s a new addition to their workflow that lets them focus on higher-value work and get rid of this terrible piece of their job.

I went to New York City recently and was put in front of Fox News, NBC, ABC and a few other huge media companies. It was awesome to see the reaction to the software from the buyers and users because it validated my initial sense that the users love and support the product. They could really see the future vision Jeff has for the product over the next 12-18 months.

3) The assets of the company coming off the back of the Series A funding of £4 million meant that the run rate of the business was strong already, so we have a good financial base to work off.

All-in-all, the culture reflects Jeff. He’s had a hand in every single interview in the company so we have an extraordinary Engineering team that I would say is more outgoing and fun than the usual Engineering team.

I can see that vibe from Jeff as an outsider sitting in your lounge, and you don’t find that everywhere!

Yes, it makes the environment more fun and enjoyable.

I had a ten-year reunion with my colleagues from SwiftKey. At first, it was bizarre to think about a reunion with former workmates after a ten-year period. But we had a wonderful time and were able to reflect on a magical experience going from zero to exiting and the journey we had. I was there for a good six years.

Things really happened for SwiftKey and we all look back fondly at that time. I feel like the same thing is happening here.

AI is a very thrown around term – a recent stat said that a large percentage of companies that claim to do AI, don’t do it!

How does Trint use AI and what does the team look like at the moment?

When it comes to AI we work within the scope of voice recognition – speech-to-text specifically.

Historically, there’s been a huge amount of money put into that sphere. There’s a ton of intellectual property that’s been crafted over the last two decades in voice recognition; primarily, a company called Nuance which has acquired these businesses. There are the obvious powerhouses in the States: Google, Amazon and Microsoft. There are also smaller players, like Speechmatics in Cambridge. From a voice rec standpoint, those are the companies that supply most of the software.

The thing Trint had to determine was if we want to solve this pain point, what’s the best way to do that from an investment standpoint? Do we want to recreate voice technology knowing that there are already major powerhouses in play with intellectual property? Or do we want to invest in how we apply it to create actual user value for human beings in this case?

If you think about it historically, a lot of voice recognition was so generic that it never really worked well in commercial settings. It’s only recently where innovations like Siri have created something that works for consumers’ daily lives. Here at Trint, we decided to invest in human beings, the workflow, the user value part of it, and not try to recreate what’s already been created.

Is Trint an AI company? The short answer is we are an applied AI company. We are the commercial application that sits on top of commoditised voice recognition.

We always think, “What kinds of added value modules can we put on top of voice recognition to make a better, more tailored user experience?”. As an example, when it comes to speaker identification, in an interview like this you can use Trint, by using state-of-the-art machine learning algorithms, to automatically recognise individual speakers.

For journalists, who would normally transcribe? Interns?

Yes, as it’s manual it would either be interns, the journalist or other human beings who are outsourced.

So, you offer time and productivity, and from a cost perspective, how does it compare?

As manual transcription is insanely expensive and time-consuming, I’d say we save a dramatic amount of time and money.

If we look at your career so far when taking a company from Series A to Series B, what are the biggest challenges and how have you approached them?

Usually, when you join a Series A company they’ve got to the point where there’s some level of chaos happening. Typically, the Founder has just come off the road from investment fundraising and hasn’t been “in the business” for a while.

What I find is all the different functional groups doing entirely different things. Some groups are being led by experienced leaders and others not. That means you have five different leaders doing five different things with five different quality levels, which is generally not a good thing.

For me coming into the business, one of the first tasks is to align that part of it. With an average Series A round, you have about 18 months of run-rate effectively, so step 1 is to say, “Look, we’ve got 18 – 24 months to get the company looking ‘like this’. If we’re going to get investment from Series B investors, the company needs to have a set of attributes that look like X. We work backward in 6 months increments. In the first 6-month period of my joining the company, we set milestones A, B and C to put us on the path to be this serious company that we’ve talked about.

This includes:

Step one aligning the leadership teams. Step two understanding the company-level strategy.

Take the best thinking in the company at the time and harvest that, both from a top-down perspective but also from a bottom-up point of view.

There are various ways you could make this happen, but fundamentally you want a company strategy that you’re personally aligned with. You want to ensure that the company understands, contributes and is embedded in it and can make it come alive, in some sense.

Once you have that clarity, strategy days and an agenda set every six months around what we’re trying to accomplish. Then every three months after that, you set your objectives and your key results processes.

A lot of companies do this and fail because of not executing properly for scale-ups, in a sense. I’ve done this three times now at SwiftKey, Signal and now at Trint. It can be highly effective if you do it correctly.

Having your three-month cycle ensures that you can look at the strategy, be informed by the strategy, and then for each of the teams you decide the best thing that can be done to satisfy the strategy from the team level and the company level.

Ultimately what you end up having, hopefully, is an OKR set that reflects the company strategy but also reflects what the team thinks is the best thing to do for the next three months, and every three months after that.

The second key job is the financial forecasting budget.

Absolutely agree. There’s a well-known statistic that 80% of SMEs that fail, fail because of cashflow issues.

Well, usually companies at Series A have quasi-budgets and quasi-forecasts. It’s very important to work with the Finance Director and the CEO to create a real-time live forecast budget that is rolling every month that the senior leadership team reviews each and every week. This ensures that as we actualise data, we can see it progress month-on-month.

We do scenario planning with cash injects, cash-burn, refinements to our headcount and how that’s going to look from a revenue perspective.

I think this is vastly overlooked by a lot of companies and what ends up happening to a lot of start-ups is they don’t realise what’s going on until it’s too late. One example is, “Have we hired too many enterprise salespeople who aren’t producing?”.

There are all kinds of things that you can get caught out on in Series A, and if you’re caught out, fundamentally, in a Series A you usually don’t have a second chance.

Being on top of your financial forecast is critically important.

Is there anything else when scaling towards Series B that you’d recommend?

Culture is the third part.

You’ve seen companies at every stage and culture can be different at every stage. What would you say are the biggest missteps when it comes to culture?

It’s crazy, every company has been so different with different sets of challenges.

It comes from the top down, which is vastly under-recognised. The CEO makes such a dramatic difference on the culture in start-up companies.

I’d say at the Series A level, you’re hitting the threshold of 40 people or so. It’s at that point the founder’s ability to be super close to everyone in the business is becoming less and less. The CEO needs to be in a position to be self-aware enough to release things into individuals and teams that he believes in.

That part of it is so critically important. If it doesn’t happen, you can write off the business. If the CEO is not willing to do that, they’re not self-aware enough to empower others.

You need to be in a position as a CEO to think about ‘CEO level things’, which is not necessarily what’s happening in the market today. CEOs need to think about the future of the company – where we need to be in 18 months, what that looks like, what the fundraising situation is, how best to treat the network that is in place, those bigger scope issues.

The other side of this has been with an engineering and data science culture at the heartbeat of all this. Some companies call these ‘hack days’ or ‘hack weeks’, but fundamentally you need to ensure creativity and innovation happens within the company. That’s what founders want, but it’s also what Data Scientists and Developers want as well, which is the flexibility and freedom and the empowerment to be able to create and innovate.

Once you’re past 30-40 people and the business becomes more commercially focussed, they feel pressure to deliver production stuff and focus on big customer account demands, feeling like they are infringed upon, in some sense.

The balance of power is that the commercial focus needs to ramp up, but you need to balance against the creativity, innovation and flexibility for the Engineers and Data Scientists to really be the full-stack people that they can be and to allow that innovation to occur. The natural question becomes, “How do you reasonably do that in a business?”.

How have you done that?

At SwiftKey, the moral I took as a template and then used at Signal and now at Trint was ultimately at the end of it. I found it to be the best solution. Once every 6 months we hold an Innovation Week. This was a whole process unto itself. The big preamble to Innovation Week was for the whole company to populate ideas of interest so we’d have a marketplace of ideas. The idea owner would pitch their idea and people would sign up for it. Once we had groups in place, they’d have a preamble as to how they’d approach it. Then Innovation Week would kick off in earnest and they’d galvanize around their concept. As a cross-functional thing we’d have marketing, product, engineering and so on, and basically do that stuff for the week. At the end of the week we’d have a big celebration and awards, and we’d do this all offsite and have it catered. It was always wonderful to see what happened. There’d be all sorts of excellent stuff.

From a business perspective, there was a good portion that was not useful or not interesting; there was a good portion that was pretty cool; and there was a band where the stuff was awesome, where the people had come up with something we never would’ve thought of. There would be some truly innovative and super interesting ideas you wouldn’t find that in the normal work environment, so then we’d look at it and put it into the roadmap or take it to one side and continue to build on it until its ready to be released.

It was cool for the company because we got tremendous ROI out of it. Equally the Engineers and Data Science folks loved the innovation, and it became the heartbeat and cadence of the company. Going from doing nothing, to doing something, to having a very mature and evolved Innovation Week process occurred over a five-year period, but it was the single most important cultural element of SwiftKey that helped us succeed. At Signal we did a version of it and at Trint we’re doing a version of it as well.

I’d say hack days with Engineering is not only uninteresting, but they also don’t work and aren’t effective. I think SwiftKey’s style is much more interesting, more engaging and useful for the company.