Q&A with Josh Beser of Away

Tell us a little about Away and your role at the company. How long have you been there, and how has your role evolved?  

Away is a global lifestyle brand with a mission to transform the entire travel experience. Right now we make suitcases, bags, and accessories designed to make trips more seamless for our community, but our ambitions lie far beyond just luggage. 

I joined the company in late 2017. I was the first lawyer and the job has changed a hundred times since then. I’ve gone from being directly responsible for doing all things legal, to leading and overseeing a team of attorneys that each focus on specific areas of expertise. As the company has grown, I’ve been responsible for establishing teams, hiring leaders, and managing functions outside of legal, such as real estate and IT, and temporarily leading other functions during times of transition, such as HR. The legal landscape has changed too. For example, when I started, tariffs weren’t a thing people talked about; today, they’re top of mind for every company that makes or sells physical products, including ours.

The company has changed significantly too. For example, I was also one of the first parents at Away. Today, we have a thriving Parents ERG (employee resource group), a bring-your-kids-to-work day that surpassed any at any company I’ve ever attended, and so much support and opportunity for people coming from all backgrounds and experiences. 

Direct-to-consumer brands need to be aware of a host of consumer protection laws (e.g., TCPA, Prop 65, FTC endorsement guidelines, state advertising laws). Other than reading Good Counsel religiously, how do keep aware of your compliance obligations and litigation risks? 

It’s a really interesting mix of legal issues—in addition to what you name above, there are also really important IP issues that flow through all of our work on the brand and product sides. In addition to reading relevant trade publications, I consistently engage in conversations with people that are working with these issues regularly, learning from them, and then synthesizing the information that is important for our business. I can’t overemphasize the importance of seeking out and building strong relationships with other GCs, with law firm partners who have deep experience in an area you care about, and non-lawyers who work in your space. Like many of your readers, we’re building our legal team while the company is growing and changing incredibly quickly, so having a broad perspective on issues—not just in our business and markets today but in the places we might grow in the next 12-24 months—is really critical.

How should founders, execs, and investors at consumer-facing brands—who might not have in-house legal support—think about staying out of legal trouble with customers or regulators? 

This is a tough question, but  -and this is not legal advice - legal issues in the consumer space often boil down to misaligned expectations. Are the customers getting what they expect from you? Is what you’re doing safe? Is it fair? Are you putting the customer first? There are obviously legal issues that can arise even when the answers to those questions are yes, but it’s a good start to look at things from the perspective of the customer. Looking at what other similarly situated companies do can also provide useful information, but if you don’t fully understand the business and legal issues that are driving their approach, it’s hard to say whether that approach would make sense for your business.

Can you give us some insight into how you choose outside counsel? Do you have any advice for first-time GCs or tech execs who don't have in-house support? How should they approach finding, paying, and working with outside counsel? 

My early in-house experience made me a firm believer in hiring lawyers, not law firms. I want to know that the individual doing our work is the best person for the job. Cost matters, too—I want outside counsel spend to be generally proportionate to the risk profile of the work. This means that we’ll have solos or small firms for some commercial agreements, specialists at a few firms for really narrow but important issues, and partners at other firms that we use for IP prosecution, litigation, financing and corporate work. 

In high growth companies, legal teams can be deceptively small because there might only be one or two in-house lawyers. In reality I’m also managing a team of sometimes a dozen or more law firms at any given time. In general, I think the highest value-add activity for in-house lawyers is advising, not drafting. So when the in-house team has to make tradeoffs for time, I’m happy to send contract mark-ups to outside counsel (typically to a solo firm or freelance lawyer) so that our lawyers can spend time advising the team.

I always want to know who I’ll call before an issue arises, so I proactively identify specialists and often engage a firm even when we have only a small amount of work for them. As we expand into new product categories and markets, I want to be intentional about making sure the right people are up-to-speed on our business before we have an urgent issue. I use a combination of TechGC referrals, existing relationships, and seeking out go-to firms for certain subject matters. One other piece of advice that I’ve followed recently is trying to get your go-to counsel approved by the carrier for the relevant insurance policy before you have a claim. Carriers are not always flexible enough to accommodate this ask, but we’ve had some success and it made a huge difference when we needed it.

How have you built and structured the legal team since joining Away? 

In general, I tend to look for in-house experience in my hires. We’re moving so fast that it’s tough to teach both the substantive work and how to do it at a high growth company. But I’ve violated that rule a couple of times in the past year for some really excellent hires, and I feel a little less strongly about it than I used to, so long as they have the substantive knowledge needed to own the work they’re responsible for.

I’m looking for people who will best support us both now and in a couple of years. It’s critical that every member of our team has a growth mindset, understands that creative problem-solving is a key part of their job (whether that issue is legal or otherwise), and feels a real sense of ownership in their work. Right now, we’re at 4 lawyers (including me) with one open role (apply here!) and we recently added a Senior Legal Ops Manager, who has been game-changing for us in a short period of time.

How do the non-lawyers at Away leverage your team and vice versa? How do you make sure that your team is not viewed as a cost-center or a gatekeeper but instead a strategic asset to the business? 

We focus on always calibrating with our teams on: our business in the next 6-12 months, the market, and the legal landscape. All three of these things are dynamic and it’s our job to partner with other teams to be on top of all of them. Decisions we made a year ago were made by an entirely different company. We have to continuously re-evaluate and make sure things make sense for where we are now and where we’re going. 

As a legal team, we really try to emphasize that our goals are the same as the other teams. We all want this company to be successful. If we’re doing our jobs right, we’re talking about balancing risk, making informed decisions about tradeoffs, and taking risks with our eyes open. 

This approach isn’t for everyone, but internally, we try to make legal generally feel cost-less financially to the business teams (i.e., we don’t talk about what it costs to use outside counsel), though we will sometimes talk through effort vs. impact analysis for internal work. My view is that I have a really tight handle on our outside counsel spend, so if we’re leveraging that expertise, we’re doing it for a reason that makes sense and roughly fits into a budget that’s already approved. In general, we also make sure that our legal team is working with outside counsel directly to keep both cost and the scope of work under control and make our team the face of legal to the company. One exception is for People Ops, who works directly with an employment group at a firm on a flat monthly fee because I’d rather that team be able to ask any question and not worry about the cost of a one-off question in isolation.

Without breaking attorney-client privilege, can you tell us about the weirdest thing you've had to deal with lately?  

It’s not super recent now, but in January 2018, a change in international regulations forced U.S. airlines to change their policies to require any lithium ion batteries, something we included in all of our carry-on suitcases at the time, to be removable. The airlines enforced the rules inconsistently—some airlines required the batteries to actually be removed from the luggage when boarding a flight, even though the rules did not actually require it—and consumer confusion was at a high point. The rule change even put some “smart luggage” companies out of business because their batteries weren’t removable at all.

Fortunately, we designed the bags to allow the power bank to be removed. However, removing the power banks in our early bags required a screwdriver, which didn’t make for a great customer experience. 

We took a novel approach to solving the problem: we gave customers three ways to have their bags retrofitted, for free, with a new ejectable battery trolley. They could mail the bag to us in a postage-paid mailer, take it to an Away retail store, or get a replacement trolley in the mail and do the switch themselves. It was an unbelievable effort that came to life (from concept to production) in a couple of weeks and solved this new pain point that was, in part, driven by a change in law. I couldn’t imagine a more customer-obsessed way to handle what was a real challenge to our business and it made me proud to be a part of a company that thinks in this way.

Q&A with Irene Liu of Checkr

Irene, thanks for taking the time!  I'd first love to know how things are going at Checkr as the company is growing so quickly.  What are some great things about the role as well as some interesting challenges? 

 Yes, Checkr is growing quickly! We’re currently serving 10,000+ customers and running more than 1.5 million background reports monthly. So the growth has been incredible. 

One of the best parts of this growth has been the increasing opportunities for me and the company to share our company’s mission with our customers and employers. Given that I oversee our legal, policy and customer education teams, I can help shape and share our company’s story and mission, which is to build a better future to improve understanding of the past. As part of our mission, we support fair chance employment and we are a fair chance employer -- more than 5% of our full-time employees are people with criminal records. To further our mission, we also create and provide educational resources to facilitate fair hiring practices for all employers and build technology to compile fairer and more efficient background checks. I’m proud that our team of compliance counsels, product counsels and customer education team can all play a critical role in bringing our mission to life.

One of the interesting challenges is staying on top of ever-changing laws and regulations in the background check industry and communicating these changes back to our customers. The background check process is highly regulated. In fact, the FCRA is enforced by two government agencies, both the FTC and the CFPB. So we (as well as our customers) need to comply with the Fair Credit Reporting Act and multiple state “mini-FCRA” laws. We’ve managed to stay on top by partnering with the best FCRA external counsels, building a robust group of FCRA compliance experts in-house, and expanding our customer education teams to help build easy-to understand content and videos to help our customers understand the laws. While this has been a challenge, our legal team has been able to add incredible value to the business and our customers by keeping them abreast of the latest legal developments.


Your background is rather unique in that you started your career in the public sector, both at the DOJ and FTC. How has your government background been an asset throughout your in-house roles?

I’ve definitely taken the path less traveled by starting out my career in the federal government. I am a public interest attorney by heart and love leveraging my government experience in legal roles in-house at tech companies to make a positive impact. And fortunately, my government experience has been incredibly useful and beneficial in my tech in-house roles. It has defined how I approach compliance and our work with regulators and policy makers.  

To truly stay ahead on compliance, I believe GCs need to think and go beyond meeting the minimum requirements of the law. With each product feature, GCs should proactively think ahead and build product features and processes that not only help your company stay compliant but also help your end users and customers stay compliant. At Checkr, we build product features to stay compliant with FCRA (Fair Credit Reporting Act) obligations and take the extra step to figure out how we can help our customers meet their compliance requirements. For example, we have built stand-alone disclosure and authorization forms in our background check application offering for our customers given the number of class actions for this FCRA violation.  Even though the stand-alone disclosures are customer’s FCRA compliance obligation, we built the feature to provide such disclosures to help our customers avoid the class action fate suffered by McDonalds, Delta Airlines, Frito-Lay, 7-Eleven, and others.

 Similarly, from a policy standpoint, I believe GCs should proactively engage and meet with relevant regulators, especially if your products are regulated. As TechGCs, we know that new regulations can potentially make or break the success of your business and your company’s new innovative ideas. So I strongly advocate at Checkr the importance of getting ahead of any issues before you’re approached by a regulator and proactively engaging with regulators. You can use the opportunity to introduce your company and your products, and potentially vet your products, influence new policies and programs, or explain how certain laws do or do not apply (or should not apply) to your product. I’ve written about these proactive government engagement strategies in my Thomson Reuters series on how to knock on government doors.

SIDE-NOTE: Subscribe to TechGC’s Jobs Newsletter for further Q&A’s like this and current in-house opportunities! 

Often startup lawyers are required to build teams without much experience in people management.  Any advice you could give to new GC's building out their legal teams?  

 People are your greatest assets on your team so as you build out your team, treat them with respect, show your appreciation, and let them know you have their back.  Invest and mentor your team members. Spend time 1-1 time with them to learn about your team member’s short term and long-term goals and find out their interests and strengths to explore where the individuals’ talents and interests overlap with business need. And remember, no one likes to be micromanaged. So give your team members space to execute and use you as a resource for any questions or escalations. And get to know them on a personal level. Learn the names of their kids, spouses, and even pets!   

 Don’t forget to also prioritize building your team culture. Share laughs, “happy Fridays” and happy hours. Be open and receptive to feedback and spend time every six months (at minimum) on team exercises to build a highly effective team. I utilize our quarterly team offsites to conduct exercises and games to not only bond as a team but help the team self-reflect, identify areas of strength and areas for improvement, and discover additional ways to add value to the organization and find ways to support each other.  

 Finally, lead by example. At Checkr, our core values include Grit, Transparency, Humility, Ownership, Connection. We hire our leaders and team members based on these values and even factor the embodiment of these values in our performance feedback. These values are incredibly powerful traits you too can leverage and embody as you build out a team: 

1.         Grit- Hustle to raise the bar, persevere through challenges and learn from failures.

2.         Transparency- Be open and trust each other to communicate the good and the bad as it relates to doing our best work.

3.         Humility- Be respectful and put the success of your teams over your own.  

4.         Ownership- Strive for thoughtful impact, and hold yourself accountable. 

5.         Connection- Genuinely care about each other and understand that our people are our power.


I understand you do a fair amount of mentoring (when you can find the time!), what are some key pieces of advice you would give to a lawyer looking to transition in-house at a startup? 

I would advise them to be patient, flexible, and open to different industries and opportunities at various tech startups. Startups typically seek lawyers willing and able to tackle new industries, laws and the unknown. They’re also looking for a lawyer who can roll up their sleeves, be a business partner, speak in plain English, and appreciate and tolerate risk. If all the above sounds interesting, I’d advise networking with startup attorneys to get to know the startup landscape and start applying! And to remember, it only takes one offer so keep your chin up and don’t be discouraged by rejection letters as startups tend to have lean, mean legal machines.  It’s a hot job market right now so keep trying!


Q&A with Ben Alden of Betterment

You've been at Betterment since 2014. How many employees did Betterment have when you joined, and how many are there today? Can you talk about how the company has transformed in the past 5 years?

I joined Betterment at around 50 employees, and we’ve grown to over 260 today. Betterment is the leading independent digital adviser, helping our clients do what’s best for their money so they can live better.

Ever since I started, it feels like we’ve changed as a company every six months. We’ve grown from managing about $500 million in assets in a single line of business in 2014 to over $17 billion today across three lines of business. We’ve grown from a team of young, hard-working jacks-of-all trades to more experienced specialists working within the established processes and infrastructure we’ve built over the years. And this has been a great thing, because we work in a very regulated environment in the investment management space (the SEC and FINRA are our main regulators), and maintaining the trust of our clients and regulators is critical to our mission and our success.

When I started, there was very little regulatory scrutiny on digital advice because the space was in its infancy. We and our competitors were small, and while the regulators knew we existed, we were a tiny portion of the investing space. As we grew and as large financial services providers began to build competing services, that changed dramatically. From regular audits to interesting issues of first impression, we are operating in a different environment, where everything is subject to near real-time scrutiny. As a result, our legal and compliance teams are formally involved in the product-building process, to help guide the team safely through the thicket of financial regulation. Our legal and compliance teams have grown to 10 lawyers today and we’re hiring if you’re interested. ;)

But throughout all this change, Betterment has held fast to its mission. Although our technological innovations have been considerable, the founding team’s most impactful innovation was building a financial services company that puts its clients first.

In addition to your GC duties, last year you became the GM of Betterment for Business. Tell us a bit about your dual business and legal role and any challenges it's created for you. 

One of the things I like best about Betterment is that I’ve been given lots of opportunities to grow and learn. It’s one of the amazing things about working at a company that’s growing so fast.

Betterment for Business provides 401(k) plans to great companies (let me know if interested!). As GM, I oversee our strategy, distribution, product, and operations teams, and generally do what I can to make sure the team has what it needs to succeed. I’m so proud of what we’re building in this space, and it’s been humbling to learn so much about different teams and how they operate. 

I am able to do both roles because we have great leaders heading up the efforts across legal, compliance, and Betterment for Business. The challenge, however, is being mindful of my role as I switch from one context (GC) to another (GM). On any given day, I may go from a meeting about how a new product interacts with FINRA regulations to a conversation about B2B brand marketing, to a meeting about our product roadmap, to an interview for a sales representative. To avoid conflicts (and to protect privilege), I’ve also asked the legal team to not treat me as a lawyer when I’m working on Betterment For Business matters, which means I often get a be a client of my own team! In a way, this has helped me grow both as a lawyer and as a business person, because I get to see the company from the perspective of each. 

It’s been an amazing experience, and I think getting this business experience will make me better in my GC role--I’m certainly more understanding of business needs and desires!

How has the legal team evolved over the past 5 years?

A little over five years ago, there really wasn’t a dedicated legal team at Betterment. But we’ve always had wonderful lawyers--including a co-founder--who have been deeply engaged in building and working on our regulated entities (an investment adviser and broker-dealer). 

I was originally hired as an operations manager and legal counsel. The legal team started when I realized we had operations covered, but didn’t have a legal department per se. It started like most of these departments do, with me covering a large area of ground and trying to understand the needs of the business. As I learned more, I realized we would need to proactively build our legal and compliance teams as part of responsibly managing growth in a regulated space.

Over time, the team grew to cover two major areas: (1) product and regulatory counseling; and (2) corporate/commercial work. The latter covers what you might see at a tech company at our size and stage of growth. The former is more specific to Betterment, and exists to guide our product, design, and engineering teams through financial regulation, to accelerate our product development and make it safer. 

We also have an excellent dedicated compliance team of lawyers to help us build and operate our regulated entities. At first, the legal and compliance teams were essentially one team, with people wearing multiple hats. As we’ve grown we’ve specialized more and expanded the compliance team. I really enjoy this part of the job, because I’ve come to view compliance as the operationalization of law.  

Betterment operates in a heavily regulated environment. Which regulators oversee your business and how have you navigated them?

Our primary regulators are the SEC, FINRA, and the DOL. But there are many other regulators we might interact with on a regular basis, including state securities regulators. 

We do our best to work constructively and proactively with our regulators, which we’ve learned helps all parties get what they need faster. We do this as they touch Betterment directly through exams and outreach, but also through advocacy and industry groups. We formed a digital adviser industry group and have found that to be a great way to discuss broader industry issues. 

For the most part, our regulators want similar things as we do: clients invested safely in accordance with their needs. So when we do right by our clients, we tend to be doing right by the rules and our regulators as well. Our legal and compliance teams reflect and believe deeply in this, and we view ourselves as builders--just like the business--which makes being a lawyer at Betterment fun and interesting. 

We both started our careers as litigators—how do you think that background’s helped you as a GC? Do you have advice for litigators who’ve heard that going in-house is better suited for transactional lawyers?

I am a big believer that litigators make great in-house lawyers at tech companies, especially younger and regulated tech companies. Someone once told me that of the Fortune 500 GCs, about half are former litigators. I’d love to find that statistic somewhere...

The job of a litigator, abstracted, is to take a client’s problem, figure out all the law that governs the issue, uncover the facts from all sources, mold the facts and law into a narrative that’s convincing to extremely sophisticated parties (judges, arbitrators, etc.), all while another smart lawyer is gunning for your work, and maybe you. You have to be a strong advocate, good on your feet and in writing, and you have to be flexible to adjust to the varied and changing cases, rules, regulations, courts, etc., you face on a regular basis. Most importantly, you have to be excellent at issue spotting. All of these are very useful skills at a tech company, especially in a regulated one, especially as the regulated field itself is developing.

This doesn’t mean I think litigators can or should do anything and everything, just that I think the cliche that litigators don’t go into in-house roles isn’t accurate or good advice. 

For litigators looking to go in-house, I’d recommend you look for regulated tech companies--even if you don’t have experience in the specific field--or tech companies that are early on, when your issue spotting abilities are critical.