Building the rocketship as you fly it: Saman Harris, VP Legal, Checkout

Hi 👋 Who are you?

I’m Saman Harris, VP Legal at Checkout.com. 

You joined Checkout.com as the Senior Legal Counsel - and now you’re VP Legal. What’s that journey been like for you?

It's been action packed; there’s always a lot going on, which is a common scenario with legal at a high-growth business. I head up the commercial legal and legal operations functions, and my role for the last year has been growing the team and ensuring we scale efficiently to support the business. When I joined we had less than 10 lawyers, and we’re expecting to reach - and possibly exceed 40 - by the end of the year. We’re building the rocketship and flying it at the same time.

How has your role changed during your time at Checkout.com? 

When I joined, my role involved working closely with the business to build on and improve existing processes - all while keeping up to speed with business-as-usual (BAU) legal work. 

Now my role has become more strategic and, as the business becomes more mature, we are looking to develop further automation and innovation to enable the legal team to properly collaborate with the business in a with a scalable legal team and sustainable and scalable way.

It's a multifaceted and demanding role, meaning it’s always important to step back and make sure you're not just focusing on the small day-to-day tasks, but also the bigger picture.

What skills do lawyers need to progress to a VP role?

You’ll always need your legal skills at a high-growth company, as obviously you still need to get the legal work done! But the transition to more of a leadership role is one where lawyers also need to build on management skills. They need to increasingly rely on soft skills to build relationships with stakeholders within the business, but also to build and develop a strong and positive culture in the legal team. 

It’s important to work cross-functionally in building a solution that works for everyone. For example, we've built our NDAs into Salesforce so the sales team can effectively send out NDAs from their platform of choice

Does that progression also mean you now have less BAU work to do? Or more?

In theory, there should be less BAU work, but given the complexities that come with hiring new people into a heavily-regulated industry and the volume of work that a high-growth company generates, there is still lots of BAU to do. 

It’s really important to ensure you take the time to train and develop new team members so they can feel confident in their role and act independently as quickly as possible. We’ve been lucky to hire some great people, which has really helped.

We still have lots to improve to try and ensure the legal team doesn’t answer the same questions / do the same tasks repeatedly, which will definitely help reduce BAU across the team. However, the reality is that it's important to keep your head above water long enough to do the more strategic work!

What does your work within legal ops look like so far?

We’ve built a team of three in legal ops and we work together to make sure we implement the right strategy and ideas.

We know what outcomes we’re striving for, and these range from: improved efficiency and scalability; better access to clean data; and making sure we can report on our metrics to the business, the directors, C-suite, and so on.

There's a large sales ops function at Checkout.com that leans heavily on Salesforce. So we work closely with them, as well as with product, to make sure we're building scalable solutions collaboratively that work across multiple teams, and not just as a solution for legal. 

It’s important to work cross-functionally in building a solution that works for everyone, including leveraging existing tools, platforms and processing where possible. For example, we've built our NDAs into Salesforce so the sales team can effectively send out non-disclosure agreements from their platform of choice without the need for legal to negotiate or be involved. 

We’ve also built (and are still developing), a self-help portal. This includes enabling the business to self-assess third-party NDAs.

In these smaller businesses, processes aren't necessarily established, there’s no bureaucracy and everything is developing and changing all the time... you have a real chance to help the business beyond the legal work you do

When it comes to legal operations, what do you prioritize? 

One of our priorities was making sure our end data was cleaner. When I joined Checkout, we didn’t have many automated systems in place, aside from a ticketing system to handle requests. 

The starting point was to make sure we used those systems correctly and started collecting data accurately. Being able to collect and present data back to the business is crucial to show the value legal adds internally. However, it is also important to help guide our own decisions on hiring, improvements, budgeting, and so on. 

The second priority was to improve how we work with the business to seamlessly onboard merchants; ensuring a great merchant experience and reducing time-to-revenue as much as possible. We’ve now implemented a tool that helps with contract negotiation, template storage, the tracking of redlines and other elements of contractual negotiations.

In particular, we wanted to automate and improve the routine contracting process, so merchant onboarding wouldn’t be such a high-friction point across the business.

We are continuing to develop that tool to have automated, built-in, negotiation and fallbacks positions. Longer term, this will:

• Take the strain off the legal team, with standardized escalation processes preventing freestyled negotiations
• Save time for the approvers outside of legal, so they could approve documents without having to go through legal and without considering bespoke drafting changes
• Enable the sales team to self-serve on as many of their deals as possible 

Whilst this will have a massive benefit for the business and for merchants, ultimately, it will also free legal up to work on more strategic matters and to dedicate more time to higher value enterprise merchants, who inevitably need a bit more hand-holding through the process.

Finally, you moved from one rapidly-scaling fintech (GoCardless) to another - what aspect of the in-house role, particularly at a scaleup, appeals to you?

I just enjoy being close to a business and (hopefully) having a real and tangible impact. In these smaller businesses, processes aren't necessarily established, there’s no bureaucracy and everything is developing and changing all the time, meaning you have a real chance to help the business beyond the legal work you do. 

In addition, it’s generally exciting and fun: you get thrown into a variety of different challenges and problems, and you need to be solutions-oriented. That's the part of the job that I really enjoy. 

I also think that high-growth businesses bring bigger opportunities; in 18 months I've gone from being a senior legal counsel at GoCardless, to leading a team of 10 - and that progression wouldn’t be feasible in a corporate environment. 

Ultimately these rapidly scaling companies bring amazing opportunities and challenges that make every day different - you always end up on the frontline of novel situations in a growing, global, business. 

Thanks, Saman!

Saman Harris is VP Legal at Checkout.com. Want to hear more from the visionaries scaling in-house legal? Join our community of 400+ lawyers and legal ops teams.