Rowan Bailey

How legal can enable sales operations

Scaling legal
December 1, 2020

How can in-house legal teams add value to sales operations when sales need it most? Peakon's head of revenue ops, Rowan Bailey, explores the different ways he collaborates with legal to get results.

This is an interview from our eBook - Revealed: what the business actually wants from legal.

When you arrived at Peakon, did you have a legal team?

I was one of the first 40 or so employees at Peakon – we’re more than 250 now. When I joined, we had no legal team – the first lawyer joined in late 2018.

Before you’d worked with in-house lawyers, what was your perception of them?

That they’re serious people. There are lots of stereotypes about the legal profession. You might think of them as being serious, stuffy, on the laggard end of the spectrum when it comes to technology, fond of red tape, risk-averse, and spending all their time poring over legal documents. That changes when you have a relationship with lawyers as colleagues, rather than as something more distant – but in any case, in my experience, those stereotypes turned out to be completely unfounded.

Sales want their contracts to fit the narrative they’ve been discussing, while legal want contracts to fit a pre-approved template. My role is to try and accommodate both

Is it a concern among revenue ops that the arrival of in-house legal might slow down the sales process?

Yes, but only in terms of adding bottlenecks – you don’t want anything throttling what you’d like to be a well-greased machine. In sales and revenue ops, you don’t want to introduce new steps into the process of closing a deal. My job is to reduce the number of steps between A and B, rather than to add them.

In your head you might lump lawyers in with finance – they both want things done in a certain way, to make sure all our documents are in good shape in case of an audit. But at the same time, lawyers bring an air of responsibility. They represent maturity in your sales process, they bring standardisation, they work towards minimizing risk.

As head of revenue ops, how and how often do you work with legal?

Contract process has been our main point of collaboration. Legal first started to support sales at Peakon to make sure that our contract process remained robust. If sales teams are editing order forms, using language that’s no longer current, or changing SLAs to fit commercial conversations they’ve had, then legal should be involved to minimize risk.

The natural tension there is that sales want their contracts to fit the narrative they’ve been discussing, while legal want contracts to fit a pre-approved template. My role is to try to accommodate both flexibility for sales and risk minimization for legal – particularly at the point of sale.

Is self-serve key to making sure legal enables revenue operations?

Yes, absolutely.

How does the legal team enable you to self-serve?

To enable us to move quickly, a majority of what we do in terms of contracts is templated. And it’s helpful that our legal team make the criteria for using boilerplate terms extremely clear. From an operations perspective, it really helps me that those criteria are rules-based, without subjective elements, so I can build a system that will primarily allow a salesperson to sell using an order form with templated terms. If they want an amendment, for any reason, then there’s a different track that they’ll need to go down.

We use ‘cases’ to alert the legal team of complex or high-value contracts that need to be amended separately to our boilerplate terms. Sales reps using that system can request support ahead of time – the more notice they can give legal, the better. They can proactively alert the team early on, if a deal is shaping up to be one that needs legal’s input.

How do you like to communicate with legal throughout that process?

It’s really important that we have one standardized channel for those comms. In sales teams – particularly when we’re in the office – it can often be the case that whoever shouts loudest, sits closest, or even works in the same time zone as the legal team ends up with the best access. In a global business with teams in different time zones, obviously that doesn’t work. Legal’s discipline and support in sticking to one channel is essential for a predictable and unbiased sales process.

In the future we’d like to standardize our entire template and use a rich clause library to map out the approved changes that sales reps can bring in for different situations.

In carrying out your role, when do you most need legal?

When there’s pushback on our terms. Legal is particularly useful when we’re dealing with enterprise clients who are trying to force their terms on us. That might mean we have to strip back everything, agree to contract on their paper and then find ways to inject our terms into the new agreement.

That’s not easy, and it takes time. But that should only happen on high-value deals – and those are the deals where you’re comfortable having legal spend their precious time helping you. Broadly speaking, legal’s involvement tracks with complexity and deal value, and that’s a judgement call they make themselves. If they have 40 sales reps pinging them messages asking for help, then they have to filter those deals and prioritize. If the legal team is proactive in hunting down complex and high-value deals, that’s a win for both teams and makes everything easier to manage.

We’re all trying to grease the wheels to make sure deals close – legal is no different to the sales team in that regard

How does legal support what you do? What are some of the areas in which you find them super helpful?

Yesterday was the end of the quarter. On days like that you see how much everyone at Peakon absolutely loves our legal team. We have a shoutouts channel in Slack for each deal, and in every new deal that closes, you’ll see one or multiple people from legal getting shoutouts for going above and beyond in getting the deal over the line.

What drives that positive sentiment?

They’re super proactive. They anticipate blockers for the sales team and try to head them off before they arise, often suggesting solutions to problems that haven’t been brought to them yet. There’s no email tennis – the legal team will often head everything off at the start by just setting out in one email every issue that might arise and their solution to it, instead of starting a long conversation.

Other times an email might not be appropriate, so instead they’re setting up a call with the other party’s legal team to get the heavy lifting done in half an hour on the phone up front, rather than dragging it out over weeks. Most of all they understand the commercial reality they’re in. We’re all trying to grease the wheels to make sure deals close – they’re no different to the sales team in that regard.

Apart from when deals are closing, when is it useful to have lawyers around?

Renegotiations with suppliers can be tricky, and it’s really useful to have lawyers supporting there. These tend to be known events in terms of timing, so you can plan for them. There’s also employment, onboarding and offboarding, establishing legal entities around the world, privacy – a whole load of stuff that happens under the hood that sales aren’t aware of, that the legal team is working through alongside all that revenue-facing work. That means that if you ask legal for their help on a sales issue late in the day and with no notice, and you get a short answer back from them, then you shouldn’t be surprised!

Salespeople like to be hugged before you tell them anything – warmth is a tough thing to coach and it’s not always the style that lawyers arrive with

Where do you think in-house lawyers generally have room for improvement?

Our team is superb, but for sales generally, communication style is something to be aware of. Salespeople like to be hugged before you tell them anything – warmth is a tough thing to coach and it’s not always the style that lawyers arrive with, depending on where they trained or worked before. That doesn’t necessarily cause problems, but it’s a known quality about each team that you need to be ready for when you join an organization with a large sales team

How can lawyers bridge the gap between the kind of personality salespeople have, and the mindset lawyers need to have?

Respect – of time, more than anything else, in both directions. Requests that pass between legal and sales in either direction are really requests for each other’s time. What you’re actually saying to your legal counsel by coming to them with a query is “Can you spend eight of your precious hours on this boring job for me?” People who understand this concept dress it up properly and do it early enough to make it manageable. That shows respect.

Similarly, in the other direction, lawyers might push back on something, not realizing that the change they’re enforcing means you have to kick off three new meetings and go back to the drawing board commercially, rewrite your pitch deck and lose momentum. That’s the fundamental exchange of time that’s happening between sales and legal, and it needs to be managed respectfully.

What kind of qualities do you think a lawyer needs to enable a sales team and not block them?

Having that entrepreneurial spirit is incredibly important, especially if you’re walking into a fast-growth scaleup environment. It’s important that lawyers understand the ship that they’re on. I don’t know if that’s atypical or not – I have a limited sample size of lawyers I’ve worked with and ours are amazing. Writing the job description to attract that lawyer is one thing, but finding someone who would gel with the company and excel there is another.

What advice would you give to a lawyer joining a high-growth scaleup and working with a sales team?

Listen to your sales team. Even if you have preconceived notions of what sales reps are like, and even if you already understand the problems they face, just looping them into your planning process will pay dividends later on. If a new lawyer coming in makes it their business to talk to the sales about their challenges, just taking the time to establish a dialogue will reap rewards.

This is an interview from our eBook - Revealed: what the business actually wants from legal. Download and find out what HR, sales operations, C-suite and more expect from their in-house legal teams.

Rowan Bailey is the co-founder of Workbounce, and was previously Head of Revenue Operations at Peakon.

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