This article features highlights from episode two of our podcast, The Abstract. You can listen to the full conversation here.
Doug Luftman has had a storied career as a legal professional and leader, working with a number of high-growth tech companies for over two decades.
“I’ve been in Silicon Valley over the last 25 years, watching it go from consumer electronics and hardware companies to software-as-a-service and now ChatGPT and artificial intelligence. It’s been pretty exciting seeing where things are going and just being part of the history of Silicon Valley.”
He had his first stint as an attorney at Fenwick & West LLP before moving on to fill a variety of legal executive roles for both private and public tech companies, including Intel Corp., Ciena, Palm Inc., CBS, NetApp, and DocuSign, among others.
"I think the work philosophy and mentality in Silicon Valley has been really refreshing. Sometimes it gets that cowboy culture, but at the same time, it's this exciting environment where you're encouraged to think outside the box. And it's not about risk elimination. It's about the assumption of risk — going in with your eyes open and just trying to make a difference."
At DocuSign, Doug served as VP & Deputy General Counsel (DGC) and Chief Privacy Officer, leading all legal matters related to product development, public sector sales transactions, IP protection, privacy, and compliance, among others, for the $2B+ legal tech company.
A little while after our conversation took place, Doug took up a role as the Chief Operating Officer & Chief Legal Officer at ScaleWith.
We spoke with Doug for our podcast, The Abstract, where we dove deep into his perspectives on finding your path and building a dream career as an in-house legal professional.
Positioning yourself for GC, CLO, and legal executive roles
Throughout his career, Doug has held various senior and executive-level titles across high-growth companies, from GC and CLO to VP of Legal and Chief Privacy Officer. He shared his thoughts about the relevance of titles when taking in-house legal roles.
Evaluating job titles and aligning expectations with your company
According to Doug, you have to have a well-rounded understanding of the role you’re assigned when taking up a legal position.
Your title defines your role and whom you report to, but it’s critical to also look beyond the title and envision your career path.
"It’s not all about the title. I think it's more about looking at what you want as a career trajectory and deciding whether you want to be a specialist or a generalist. Being a generalist means you need to think about the bigger picture. You need to be able to connect the dots between different functional areas within a company, whether it's product development, corporate compliance, sales and marketing, government affairs, and the like."
Your title and who you report to can also tell you a lot about the perception of your role, and of Legal itself, within the company you choose to work with.
“Titles and reporting structure can be insightful as to how the business perceives Legal or the type of individual they want to hire. ‘Head of Legal’ or ‘VP of Legal’ often suggests they're looking for someone a little less senior and maybe more on the operational side. Those titles also often report to the CFO. But when you see a GC role that’s reporting to the CEO, that’s likely to be more of an executive role viewed as a peer to the CFOs and COOs.”
Building a strong executive presence
It’s imperative to gain visibility and credibility with the executive team to position yourself for a legal executive role. Take the time to understand the business and the leadership, learn what makes them tick, and collaborate how they prefer to collaborate. Then, identify your strengths and broaden your skill sets.
“If you're a VP of Legal, there is a chance that someone's going to be put above you later on if you don't establish your executive presence. And if you're the GC, you’d need to step up to that executive role, too.”
Developing your skill set as a generalist
The most successful legal counsels have one thing in common: They're generalists. As Doug said, you need to think of the bigger picture and make yourself pivotal to various operational units of your organization. This may include taking new courses, doing more research, or getting involved in activities that generally expand your skill set.
“Pick areas that are truly your specialties and refine them. Identify areas of need, and keep developing until you build enough skill sets to show that you can basically tackle all the things that a company needs.”
Heading into an environment that gives you space to thrive
Your work environment and the people you surround yourself with are critical to your success.
During our conversation, Doug highlighted the importance of having the right managers and mentioned some of the things to look for while choosing a company.
Choosing the right company
“I think what you're always looking for is a company culture that encourages professional development and career growth. Often, people look at companies just from a point of view of its name. But there are many companies out there that you could probably name, where the work culture does not necessarily fit the public persona they’ve maintained.”
It’s important to consider your options holistically, instead of automatically going for big-name companies. Evaluate every opportunity and ensure that your chosen company complements your career objectives.
The role of great managers and leaders in shaping your career
Doug attributed much of his success to his relationships with his managers and mentors.
“I've had this really fortunate opportunity throughout my career to have very dynamic and supportive managers and mentors who always wanted me to get additional skills or insight.”
Great managers and leaders promote growth within their teams, helping you become more productive, gain exposure, and hit your career goals. On the flip side, if your company has toxic managers and leaders, there's a high chance you'll struggle in your role.
"I think an important piece to consider is the sophistication of the leaders and the executive team that you're going to be working with, because you'll be working very closely with them on a regular basis. And if their personality and work philosophy don't align with yours, there will be additional friction, and there's just no need for that friction."
Working in industries or ecosystems that align with your goals and personality
A big part of choosing a home for your legal practice is understanding the environment and industry you want to work in.
“Over time, you start developing a broad brush type of expertise across multiple industries so that you can be a utility player, which is often how I operated. Others may want to specialize in specific ecosystems, such as fintech or medical devices and the like. So you need to understand where the company fits in the overall ecosystem, and if you like that type of environment. Because every industry has potentially a very different personality to it and a very different potential business motion. You have to make sure you align there.”
Doug emphasized on the importance of keeping up with trends and being forward-thinking when choosing an industry.
“If you talk about certain technologies that were around 20 years ago, they have either gone extinct, gotten commoditized, or are struggling today. This is because there's a beginning, middle, and potentially an end to a lot of industries, or at least a revolution when new disruptive technologies and business models come in.”
He recommends talking to people who are already in the industry. This enables you to gain insights into the intricacies of the ecosystem and determine if its dynamics align with your career goals.
Seeking holistic mentorship and building on feedback
Mentorship is critical to growth in any field of work — but especially so in a dynamic field like in-house legal. Access to knowledge and experiences of others can help you successfully navigate certain areas of both law and business, and overcome professional hurdles.
According to Doug, you must be curious and never afraid to ask questions.
“If you think that you're doing everything perfectly, you're not going to grow. There's always an opportunity for self-improvement.”
And when trying to identify these areas of self-improvement, multiple perspectives can go a long way.
“It's always important to try and get every angle that you can. Get mentorship and insight from managers, people who report to you, and also people that are comparable within or outside the legal group. Really try to get a sense in different ways."
Building a presence in front of executives in your company and seeking constructive feedback will also help you hone your skills and position yourself for leadership roles.
“Get feedback from CEOs and boards; learn what makes them tick, what's important to them, and what isn’t. If you did a presentation, ask questions like ‘What resonated?’, ‘What didn't resonate?’, ‘If I could do it over, what should I consider?’ Be curious about how to improve and find the right people to get feedback from. I think that's invaluable. Because then, based on the type of individual who comes in, you can tailor your advice and change how you convey information.”
Hiring, managing, and retaining top legal talent
For leaders and managers, finding and retaining great talent can be challenging. Doug offered some important tips and insights from his experience building and managing several high-performing legal teams throughout his career.
#1 Be genuine and authentic
To begin with, Doug emphasized the importance of being genuine and open with your team.
“If you're approachable and people feel like you're trying to do the right thing, people give you a little bit more discretion if you goof up on something as a manager or do something that rubs someone the wrong way.”
#2 Build a high-performing team
The next thing to do, according to Doug, is recognizing where you are lacking and building a team that can help you fill in those gaps, instead of always trying to be the most intelligent person in the room.
“You want to surround yourself with people that are the brightest and the best around you, and who just put you to shame. Bring in people that will give you their insight and tell you when you're wrong or when there are alternative ways of doing things. You want to ensure you have that kind of a team.”
#3 Empower your team and build towards their success
When you build a team of high-performers, it’s also critical to allow them room to grow and empower them to achieve their goals.
"You have to recognize that you can't just put them in a very narrow box and say, ‘I'm only giving you tactical stuff, and that's it.’ You have to balance it with empowering them to present to the CEO and the board, empowering them to drive strategic projects, and making sure that when you do give them those opportunities, they do it when they're ready and prepared to succeed."
Your goal as a people manager is helping your team grow and take on greater opportunities and challenges. However, Doug emphasized the need for transparency, especially with employees yet to attain the level of preparedness required for specific opportunities.
“Be transparent and say, ‘Look, I'm not giving this to you right now, not because I think you're going to muck it up, but because I want to make sure you look like a rockstar in front of this executive or this individual. So, let's hold off for three months or so, and I promise that we’ll work on it, and I’m open to having conversations with you.’”
#4 Provide feedback and organize 1-on-1s
“I'm a big proponent of making sure that people know where they're just hitting it out of the park and where there's an opportunity for further growth. Part of the role of being a manager is to make sure that everyone's successful.”
To this end, Doug believes in providing continuous feedback and holding frequent 1-on-1s with his team. He acknowledges that while not everyone appreciates such meetings, they can help set people up for success.
“My philosophy is that you should never go into a performance review where your team doesn't know where they stand or where they're strong and where there's opportunity. That should just be a validation of what's going on. All too often, people are surprised by the feedback they receive, because it hasn't been this ongoing dialogue through the whole year.”
Building trust and credibility with cross-functional teams
Legal is often viewed as a blocker within companies, largely due to friction between the legal team and cross-functional teams. To eliminate this friction, Doug recommends approaching this problem empathetically.
“The first step to building trust with cross-functional teams, from senior executives to your peers to more junior individuals, is recognizing that not everyone has interacted with a lawyer in the past. Or if they have in the past, they may not have had the most positive experience.”
Business teams often don’t understand the value that an in-house legal team brings to the table — and it’s up to you to educate them and showcase your impact in their language.
"The biggest compliment someone on my team got at one point was, ‘Why do we have a lawyer at this meeting?’ And that opened up the opportunity for them to say, ‘Well, I'm a product attorney. And I'm here because, to give you product legal advice, I need to understand the product, the technology, the roadmap, the ecosystem, and everything else.’ It provided that opportunity to explain the role, how they're curious about what's going on and, most importantly, that they care about what the client or business partner is doing."
This way, you become more aware of the legal needs of that business and can make more valuable contributions instead of staying boxed in within your department and working in a silos.
“Ultimately, if you detach yourself from the business and only engage to answer questions, you end up becoming an ‘ivory tower of no’, where you only stop deals from happening and don't understand the context around the advice you're giving. You want people to think of you not as a lawyer but as their business partner who happens to have legal expertise.”
Expanding your role and getting exposure to different areas of the law
Throughout his career, Doug held multiple roles — from VP and DGC to Chief Privacy Officer, Chief Innovation Officer, and more. He explained how he built the requisite capabilities through years of active exposure to business operations.
Identifying opportunities and taking ownership
A large part of Doug’s success throughout his career may be attributed to his ability to identify gaps and take ownership.
“Whatever company you go to, go in with an evaluation of how you can make a difference. What are the needs within the company, and is the company receptive to those needs?”
If you spot a problem, even if it's not directly related to Legal, call it out with the leadership and view them as potential opportunities for growth.
"Over my career, I've seen areas — whether it's new product introduction, advancement into new countries, or other operational processes — that have no direct connection to legal roles; but to get to the legal advice, you need to involve yourself in the business strategy and the decision-making process, as well as the process of implementing that strategy."
Understanding business needs and filling gaps
“I think one of the reasons why I went to DocuSign to begin with was the opportunity to stretch into different areas, start connecting all the dots, and build out an infrastructure.”
At DocuSign, Doug built out a government affairs team since the company had begun dealing with many public sector contracts.
"There was a huge need for government affairs during the pandemic. We made a recommendation to the CEO, saying that there will be a lot of public sector needs, so we need to build a government affairs function to engage with the public sector."
Similarly, with privacy and compliance, there was a need to centralize these functions and create dedicated teams to tackle issues holistically.
“Legal has the ability to see horizontally and cross-functionally across the whole organization. Because of that, you can see where things are working really well and where there's opportunities for further enhancements. I think there are opportunities for lawyers to step up to the occasion when they see something that isn't working well. Especially as you want to be perceived more as an executive leader.”
The role of legal tech in enabling modern in-house lawyers
Doug identifies himself as a legal tech nerd, having played within the industry for over two decades. We went into how the industry has evolved and how it’s helping legal teams bring more value to their companies.
The evolution of legal tech to what it is today
According to Doug, legal tech has gone through at least three phases.
“I think the first phase was between the late 90s and early 2000s. There were separate corporations building their own legal tech internally, having their own IT groups build out systems because there just wasn't anything commercially out there.”
Companies in this era had to develop strategies for scaling, and these paved the way for the advent of commercial tools and the second phase of the legal tech evolution.
“The first set of commercial tools were really clunky. And lawyers were usually picking the best of the worst just to get things done. But at the same time, they got a taste of how tech can make them more optimal and efficient.”
Now, Doug believes we’re in the third phase, characterized by next-generation technology and a team of developers who truly understand the pain points associated with legal roles.
“What’s exciting is that now there's a lot of companies, such as SpotDraft and others, bringing in the next generation of technologies. And the people that are designing them actually know what Legal needs, both internally as well as for outside counsel, and are being very sophisticated with it.”
Gaining competitive advantage with legal tech
The legal tech industry is rapidly expanding and companies are beginning to see its importance to legal processes, from contract management to billing and research.
"I think we're getting to this point in the legal tech evolution where legal tech is no longer a weird little area where people hold their noses and use whatever's out there. But rather, it's actually offering strategic tools that are not just value generators for the legal department, but are also becoming product differentiators and a competitive advantage for companies."
According to Doug, tech helps companies move faster in their industries, cover more ground, and get better market share.
"If you can pull up an agreement very quickly or respond to something more decisively than your competitor, you're able to get into a new market quicker or build a product more rapidly. Furthermore, if you can give insight to the board or the CEO faster, the company will also move at an accelerated pace, which I think is what we all want to do."
Navigating the impact of layoffs in the legal industry
Layoffs are difficult, but common in the modern world of business.
How should a legal counsel react in the face of layoffs and unexpected career transitions? And how can they bounce back stronger? Doug offers his views and advice on this.
#1 Understand that layoffs don’t define you
The key to staying motivated is understanding that getting caught in a layoff doesn’t mean you’re worth less than others. There are many things that influence a company’s decision to downsize.
"The key thing is it's not a reflection of you as an individual or as a professional. Layoffs technically occur because the company eliminated a position. Some people are fortunate to find a new opportunity immediately, while it takes a little longer for others. That's also not a reflection of the individual, but rather of the opportunities out there, your network, and other situations and dynamics going on."
#2 Surround yourself with the right people
Doug stresses the importance of reaching out for support at such times and surrounding yourself with people who understand the dynamics of the current market.
“Reach out to family, friends, and colleagues, have conversations, and validate what you're feeling. Then, it comes down to powering through the dynamics of looking for your next opportunity and looking at it from the view that the next opportunity may potentially be a better one.”
#3 Use the time as an opportunity to grow
While you’re looking for your next opportunity, Doug recommends taking some time to reevaluate yourself.
“If you have free time, do additional things like learning the guitar or improving your golf game. Take courses or lectures, like listening to this podcast here, and really use it as an opportunity for growth.”
To hear more of Doug’s insights on achieving success and thriving as an in-house legal professional and leader, listen to the full conversation on The Abstract.
