James Osmond, Triptease COO, shares his thoughts on choosing the right VC and expanding sales in the US...

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Q: What advice would you give to founders who’re raising capital?

A: Raise more than you think you need to because of the time and resources it actually takes to raise capital. I remember when we closed our Series A, figuratively holding the cheque in our hands we were screaming with delight. It dawned on us in the same meeting that we hadn’t raised enough money and that we had to go back out to our investors and ask if we actually could double it! This then took another 3 months of our time and resources.

My one bit of advice on the fundraising process is being true to yourself and who you are and what kind of company you want to build.

I’ve met investors who said: “We like you but we think you are too ambitious and you want to hire too many people to quickly.” On the flip side of that I’ve also met investors who said: “We like you and we can see how you get to be a £500m / £1bn company, but we can’t see how you get to £2bn.”

You go through these extremes when fundraising. Someone wants you to go slower, someone else wants you to go faster. What I learned from that was that the really important thing is to get a funding partner onboard who is aligned with what you want to build. Don’t change your pitch to fit in with the different desires of VCs. Make sure they are aligned with the team you want to hire, the pace you want to go at and what the end destination looks like.

Spending time thinking about that is going to lead to a better board and improved process.

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Q: Would you do anything different? What do you wish someone had told you before you did you first fundraise?

A: Patience. You’ve got to kiss a lot of frogs. We spoke to a lot of VCs in both the UK and the US. We had at least 40 meetings with VCs before getting to a term sheet.

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Q: What has it been like to expand internationally and manage a second office?

A: The difficult thing is building one culture across two different offices. The only thing that matters is that it’s not about managing culture, but investing hard in culture to get real teamwork going.

As an example: for the last two years around Christmas, despite our cash balance nearing an “exciting” stage, we have brought the whole team over to Europe (Barcelona and then Paris). We think it is important to invest in our team and get them to meet face to face as most of them will have never met each other. Getting time together leads better teamwork outcomes. You have to show that you believe in creating one single culture.

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Q: When do you think about the US?

A: Getting a return on a B2B investment is about thinking American. Be as American as possible as early as possible. My last business, before starting Triptease, was a global marketing consultancy and we made all of our money in America. You can scale so much more quickly.

We started our first office in New York within three months of getting our first customer in the UK and my brother moved over to the US to accelerate the growth there. I moved in to manage EMEA at that time.

If you want to go fast you have to go early. We moved two of three co-founders - including my brother, Charlie - over to scale the business in the US. You don’t have to have US revenue, but you need to have interest. If not you’ll struggle to get good sales talent.

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Q: What are the best practices when hiring sales teams?

A: Most sales people sell over the phone. I’m amazed at how few companies actually make sales reps sell to them over the phone. This is what SDRs do and you need to hear them pitch.  

Also — tell them where they are going wrong, in the interview. Give them specific feedback, finish the interview and get them to pitch again. If they have learnt and adapted their pitch based on the feedback you’ve given them, you know you can teach them to become really good and that they have the right attitude.

Finally, hire a good (and most likely expensive) VP of Sales early. If they have the right experience and attitude it  helps accelerate the whole business, which makes so many things a lot easier.

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Q: When do you decide on whether to invest more in people who are struggling versus letting them go?

A: It depends on what level you are hiring for. For junior people: Are they smart, industrious and hungry to learn? At a senior level: Do they scare me with how good they can be and much better they are than I am? That’s really hard because you’ve got to accept that you cannot be awesome at everything.

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If you want to know more about expanding into the US you can read more in Notion’s Crossing the Atlantic series, with perspectives from entrepreneurs, VCs and industry experts.