Sharan Kaur has a 360-degree view of the legaltech market. Sharan has worked as a lawyer in both private practice and in-house, as a tech buyer and vendor and as a consultant advising start-ups as well as legal teams regarding legaltech and process optimisation. On the vendor side, Sharan has worked at behemoths like Thomson Reuters Contract Express as well as fast growth start-ups such as Bryter.
Sharan is passionate about process optimization, whether it’s helping a legal team map their current working as a means to help rethink what they do and how they do it, or helping start-ups build scalable processes that help them grow.
As a founder herself, and an investor, Sharan also brings her own entrepreneurial and investor experiences to these interactions.
How did your career begin?
After completing Bar school, I began my legal career, working in-house and in private practice, advising companies on matters of corporate law and governance.
During that time, I became very aware of the many process inefficiencies core to modern legal work.
In some cases, it was simply that there were legal professionals tied up doing non-legal tasks better suited to other business professionals.
In other cases, there were legal tasks being done by legal professionals but in highly inefficient ways.
Added to that, there was never any real time management information about the legal team and their processes, so it was difficult to analyse what was working or not working in terms of the status quo.
This is when I first became interested in the business of law and how process improvement can drive efficiencies within legal.
Becoming more interested in the business side of law I opted to do an MBA at Henley Management College. I completed my MBA over several years alongside working full time. This experience affirmed that I was less interested in the technical side of legal practice advising on legal issues, and more interested in the business side of law, helping to improve the delivery of legal products and services.
Around that time, I started my own company, a management consultancy. That business tied together these various interests and my studies at Henley.
My focus in those consultancy engagements with in-house legal teams was operational excellence across the board and not limited digital transformation. I started working with legaltech, and the utilization of general tech, to reengineer business processes. In a lot of engagements my focus would be first on helping the client understand and document their existing processes and dissuade them from automating things for the sake of it. Automating a bad process is not an improvement, but can make things worse.
Through that experience I was approached to join the Contract Express team, which had been acquired by Thomson Reuters. I joined them as a senior strategic sales specialist, covering EMEA.
After 2.5 years with Thomson Reuters, I joined Bryter as their Head of Sales and Strategic Partnerships, again working in the automation and process optimization space using legaltech. But after a year and a half there I decided I really wanted to get back to running my own business again, which is what I’ve done!
How did you come to that decision, to return to consultancy?
For me, through my various roles to date, it’s become apparent that the challenge in legal is not the lack of good tech options, but knowing what to do with it.
That got me thinking about where can I provide the best value, which led me to decide that rather than selling legaltech, I’d deliver better value to customers by helping them think through their process optimization challenges more broadly, and whether and to what extent they should consider a variety of different improvements, some with tech and some without tech.
Returning briefly to the start of your career, how did you find that initial transition from legal roles to your first commercial role?
I didn’t find the transition particularly difficult; I think because I always had a very commercial mindset. As a lawyer I would frequently identify inefficient processes and try to find solutions that improved efficiency. Sometimes it went well, sometimes it didn’t – there was a lot of trial and error, but that’s how you learn!
I’d also say that I enjoyed the transition. I say that because moving into the commercial side of a legal practice, and focusing on process improvement, is where my passion lies.
Where I got stuck as a lawyer was that the emphasis on process optimization wasn’t incentivised, nor a priority.
As a lawyer you’re incentivised to bill more and record your time rather than spend usually non-billable time trying to optimize processes, even if the result of doing so is to reduce non-billable admin tasks and make space for more billable work. So, in a lot of ways the business model was limiting, and being in a legal role I didn’t have the incentives or bandwidth to spend more time on the process optimization side of things, which I realised more and more was what I really enjoyed thinking about.
It wasn’t just my experience either. I had friends in private practice at top firms, who were experiencing the same conundrum where everyone was too busy to focus on improving their processes. This is also going back a few years now, to a time when concepts like leverage and gearing, i.e. number of junior resources to senior resources, were still in their infancy in terms of implementation and understanding. The general approach to legal process and bandwidth problems were usually more about bums on seats, being busy and hiring more people when demand outstripped supply rather than finding ways to be more efficient and deliver more for less.
Unfortunately, this remains the standard thinking in a lot of legal organisations today. We have seen an increase in the number of lawyers affected by burnout. Where firms or teams cannot add more resources, lawyers and other legal professionals are expected to soak up any new work that comes in.
Which lawyer skills were transferable and which needed adaptation when making that transition from a legal role to a commercial role? Were there any other blockers?
One of the surprising challenges of moving to a commercial role was not being seen as a lawyer anymore. One day you are “one of the lawyers” and the next you are not. I have had conversations with other “recovering lawyers” who have found the same, in particular those of us who identified strongly as lawyers for a long time.
Of course, in sales roles, including when I sell my consultancy services, I am there to sell, but I am not selling in a vacuum. I have credible first hand experience of the challenges and opportunities within legal practice, having been a practising lawyer. This certainly helps with getting lawyers to share their challenges because they understand that I’ve experienced the same pain points.
In terms of transferable skills, I’ve found my negotiation and attention to detail important to commercial roles. To drive change or to sell people on an idea, product or service you need to convince the decision-maker, perhaps the CEO, to write a cheque and / or support that decision with additional resources.
Being a detail-oriented person can support that skill too. You need to know your numbers and arguments to convince stakeholders to take a particular decision or avoid a bad one. It also helps you be prepared, to anticipate questions and have the answers ready should those questions arise in regards to your business proposal, product or service.
Having an acute understanding of the value of lawyer time is certainly helpful. I’ve sat through many product demos whereby the presenter has spent too much time trotting out a standard deck, sales pitch or stumbling through disjointed and untargeted discovery questions, only to request a follow-up session to go into even more detail about this or that.
If someone tells you they only have one hour to get to know you, your product and how you can help them, you need to be exceptionally targeted and well-prepared for that hour. If you can’t demonstrate your value in that hour, you probably won’t get more time with that person. Recognising this and being good at managing time and information is crucial, and again another legal skill that is highly transferable to commercial roles.
How did you find moving into the sales role at Thomson Reuters? Obviously, you were selling your consultancy services before that, but moving into a senior sales role within a huge organisation like Thomson Reuters must have been an exciting challenge.
Yes, it was a very different experience!
First, it was working in a mammoth organisation, that is Thomson Reuters, and understanding the workings of that organisation from a team, department and function perspective
Second, I was attached to their ContractExpress product, which was a product they had recently acquired. Notwithstanding the acquisition, ContractExpress was much like a start-up within its much larger parent organisation.
There was quite a lot to get my head around with regard to those two facets of that role. The multiple layers of bureaucracy was something I had to get used to. On the sales side, I was already used to selling my consultancy services so there was little adjustment needed.
Having said that, there was a big difference in the approach to sales, i.e., between selling consultancy services and selling an established product.
ContractExpress is a powerful tool once you’ve learned how to automate documents. The challenge was getting prospects and customers to think about the documents that are worth automating and the benefits automation could bring if realised within their organisation.
One challenge is that when lawyers hear automation and time saved, they equate that with fewer billables and therefore ask, “why would I cannibalise my top line?”. In a lot of law firms, that objection is still a challenge.
But the teams that “got it” really saw the big picture, for instance Clifford Chance has a team in India that works with ContractExpress on really significant projects that deliver huge value to their clients, and free up lawyer time to focus on more complex work.
The challenging sector was the mid-market. In the mid-market budgets are tighter than at larger firms who have bigger budgets and therefore greater willingness to experiment with legal technology.
Sometimes you would also run into challenges with the smaller firms whereby they would see Magic Circle firms listed as customers and automatically assume they couldn’t afford document automation platforms, both in terms of licence and total cost of ownership once you factored in training, headcount, document automation specialists and so on. In many cases this was an incorrect assumption.
Some market segments are harder to sell to. On the one hand firms wanted credibility evidenced by peer firm clients. On the other hand, if those peer firms were too many notches above their own standing then they would assume – incorrectly – the product was the preserve of only the most elite and well resourced firms.
Were there specific differences between selling consultancy and an “off the shelf” product like ContractExpress?
Yes, there are. When you’re selling consultancy, you bring an understanding of the wider ecosystem that operates within organisations and between the different departments within organisations.
The first few weeks of a consultancy engagement will often be discovery and observation. This will involve identifying and speaking with the relevant stakeholders and process owners to understand how they work, why they work the way they do, with whom they work and what they think of their current setup and some early indications of their top priorities for change. You can’t improve what you don’t understand or know, hence this is such a vital activity to do well from the outset.
So selling consultancy is an ongoing transformational process, whereas selling a product is relatively more transactional and much less process laden. You’ve often only got an hour. Within that hour you need to identify the problem, understand the need, demonstrate value and if all goes well, agree on the next steps. You don’t have the luxury of digging deeper into the wider ecosystem of that prospect. Instead, you have to be targeted and efficient with your discovery questions – you need to assess whether the prospect is genuinely interested in buying, and has a genuine and qualified need.
This is where my prior consultancy experience has been very helpful. Because of my varied consultancy work, working with legal teams ranging in size from sole practitioners to international law firms and large in-house teams, I am able to ask right questions quickly to gather the information I need to determine whether or not the prospect is a fit for the product, or in other words, is this conversation worth their time? If it’s not, it’s best to be upfront rather than get bogged down in a product pitch and a demo that doesn’t solve their needs.
Being able to do this was very helpful when selling products; it helps you quickly triage prospects into useful categories that can make you more efficient at being able to help them, which in some cases may be pointing them in another direction.
One question I like to ask is “what’s your current tech stack?”. It’s designed to confirm the audience’s level of tech expertise. If they don’t know what the term means, it’s usually an indicator that they are coming at the product from a less technical frame of reference. That’s fine, but it allows me to quickly tailor my approach.
After your time at Thomson Reuters, you moved to another product based sales role, this time at Bryter, a fast growth automation start-up. What were the challenges and opportunities joining a fast growth start-up like Bryter and how did it differ from Thomson Reuters?
Since doing my MBA I knew I wanted to work in a fast growth start-up environment at some point in my career. I certainly had that experience at Bryter.
When I joined Bryter they were around 55 employees. By the time I left there were over 100. They grew really fast, and look set to continue that trend.
There were many opportunities and the chance to get involved in a wide variety of activities, including some I’d already been doing via my consultancy.
The activities were around product development, gathering and understanding functionality requirements, helping design and test product features and align these with marketing and sales. I worked with the development and integration teams closer than I had in any of my previous roles.
Given Bryter’s nature as a process automation platform it was also great fun working with clients to explore and push the limits of the platform and to find workarounds and solutions that achieved their desired result.
In terms of challenges, like in many of the start-ups I work with, what some people regard as challenges might be for others, opportunities. You’re expected to wear many hats from sales right through to testing new features. These challenges and opportunities are common in any fast-growing tech company. Decision-making can slow down where individuals aren’t 100% certain as to their own authority or that of others in a given situation. Part of it is very human as well – nobody likes to deliberately step on their colleague’s toes especially if decision-making remits are not clearly defined as a business grows beyond its original configuration.
It was great seeing these challenges overcome by pulling in the right people, and expertise, to organise and scale functions coherently. There are now VPs for the major functions and it is much clearer who needs to decide what, when and why. As any startup grows and scales, functions and roles become more defined with clear reporting lines.
I’d also say that in start-ups it’s often desirable for people to wear many hats early on, and to some extent that means sharing hats. It can get a bit muddled but ultimately, it’s how you remain nimble and flexible. For some that can be an exciting function of working in a start-up, it certainly was for me, but for others it can be quite intimidating and challenging!
You also advise start-ups and related organisations in the legaltech space, for instance Capacity (a practice management start-up) and The Legal Technologist (a fantastic online legaltech magazine). How do you go about forming these partnerships and what is it you enjoy about these activities?
I’ve been very fortunate to have built a good network via my consultancy practice and LinkedIn. I regularly have start-ups reaching out asking for advice, for instance, to provide feedback on their product or pitch etc. Likewise, I’ve had intros to law firms and in-house legal teams approaching legaltech for the first time or at the other end in-house legal operations teams embarking on large-scale digital transformation projects.
I’ve also started posting more regularly on LinkedIn, providing concise insights and actionable advice to share the knowledge I’ve learnt and continue to learn from the various interactions I have via my consultancy and prior career experiences. That has generated a lot of interest in the work that I do, my skillset and experience, which again has led to more introductions and opportunities.
Start-ups in particular sometimes get stuck between having a great idea that has gained traction and how to productise it or take it to the next level. Sometimes it’s simpler, for instance, wanting advice on how to hone their pitch or their demo skills.
My experience working with Thomson Reuters and Bryter is particularly instructive. I have had conversations with a myriad of legal buyers, and through those conversations I have a detailed understanding of their tech needs. Sometimes, start-ups struggle to work out who to connect with, who the right buyers are and how to uncover their needs, which is where I can help with filling in the blanks.
Initially I did a lot of this type of consulting as a gesture of goodwill, but I was getting inundated with requests so I decided to add this as part of the consultancy work that I do, in particular with helping start-ups build out their business procedures, sales processes, pitch decks and so on, always with a view to how these will scale as the business grows and secures investor funding.
That’s a snagging point for a lot of start-ups: designing processes that scale from one growth stage to the next without hindering growth by being overly process driven too soon, but having “just enough” process and structure that will grow with the business.
My advice to start-ups is that as your business grows, you will need to think about articulating your mission, vision, and setting out your strategy and objectives. More specifically you’ll need to think about process design and optimisation across all functions of your business. This is important if you want to get investors onboard, who will absolutely want clarity on these questions and demonstrable evidence that you can scale.
I am also an investor in start-ups, so I also look at things through that lens when advising start-ups, thinking about how I’d assess them from an investment perspective and suggest where they have gaps to fill.
Sometimes where I’ve been able to add value is simply by providing an objective external viewpoint. For instance, I was helping one start-up with their product development questionnaire intended to solicit feedback from users to inform product direction. The questionnaire had been set up so that the skip button was on the right side of the screen and the next button on the left side of the screen. In most cases, this positioning is reversed, so I suggested they reflect what most users are used to. What seemed like an inconsequential detail to an inward-looking team seemed very obviously back to front for an outsider like me. Changing this small detail made their feedback questionnaire completion rates improve.
In some ways this is an emblematic example of a major area of improvement for a lot of legaltech start-ups: making things easy.
Consumers want easy and frictionless products that require as little training as possible and the shortest time to value. In our personal consumer lives this sort of experience is increasingly common as product companies have invested huge amounts of talent and money into UX, UI and excellent product management. In a lot of enterprise tech, particularly legaltech, there has often been less emphasis on look and feel of the product. Lawyers want to use technology at work that has the same level of sophistication as the tech they use in their personal lives. As a result, I always stress the need for start-ups to remove friction, whether it’s in terms of their product, their sales process or something anything else.
Make it easy for buyers to buy and users to use!
What tips would you give to anyone thinking of making similar career moves to your own, for instance moving from a legal role to commercial roles and / or starting your own business?
You’ve got to see yourself in a bigger role than just the role that you’re doing right now.
If you want to do a more commercial role than the one you are currently in, make it your job to find ways to gain commercial experience within or outside your day job.
That might be doing an MBA as I chose to do, but equally there are many fantastic alternatives and shorter business courses you might consider. The key thing is to find ways to acquire commercial experience and leverage that into the role you desire.
One thing I would caution is that once you leave the law it is harder to go back. It’s by no means impossible, and depending on how long you’ve been away, you may need to work harder to convince someone that you are committed to legal practice. If you really want to quit the law and do something else, be very sure that is the decision you want to make, and that you make it for the right reasons!
One intermediate way to gain more commercial experience alongside legal practice is to move in-house. If you move to a good in-house team you will gain a lot more exposure to the commercial side of legal consumers, i.e. the business folk that such in-house teams support. Moving In-house will provide you with more scope to work on process optimization projects, in part because legal is usually seen as a cost centre by the CFO, so there is incentive alignment to optimize legal processes. Tied to that, the day-to-day in-house legal decisions are more closely related to the business decisions, e.g. What is the legal position of decisions taken?
What books, resources, podcasts or other media would you recommend to folk interested in legaltech and the other topics we’ve discussed?
I mainly find value in business publications vs. books. I enjoy Brian Solis WTF: What’s the Future? Brian talks about digital disruption and what it means for businesses of the future. It has informed some of my thinking around disruption, innovation and how tech influences and impacts our day to day.
The main publications I subscribe to are the newsletters of McKinsey, Harvard Business Review and MIT. These cover a wide variety of topics and often include the latest thinking on business, change management, tech and adjacent topics, often with case studies and supporting data.
I also enjoy The New Yorker. It’s not legaltech specific at all, but I find the topics they cover and the manner in which they do so help me see things in a different light. For instance they did a great piece about the unionization of Amazon fulfilment center workers in Alabama. It made for a really interesting read on how companies treat their employees, what makes them happy or unhappy in their role and how they perceive their role vs. their organisation’s perspective of their role.
Interested in legaltech careers like Sharan’s? 
See here for our legaltech careers guide for advice and tips on the roles, organisations and routes into legaltech.
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