10 minute read
Command of the Field
The Precision Plays that Shape a Career
By Ashley Dahlberg
I feel like I can tackle big, big things because I can see the route.
Seeing the Route
I am sitting with Elena Villaseñor Sullivan at a local coffee roaster, as pinball machines ding and flash around us. Elena’s two requests for our meeting were, above all else, very good coffee and not having to decide on a location. This reflects the type of decision-fatigue that overperformers will immediately recognize. I suspect that despite her having had a lifetime of serious titles (General Counsel, among them), Elena will enjoy the irreverence and novelty of this spot. Thankfully, I am right. She’s also not above laughing at herself. She arrives at our interview in the wide-leg, high-waisted jeans that are popular now. “My daughter said these jeans are in style,” she says, looking down in dismay at the same style of pants she may have worn in high school.
We start talking about football and my newfound understanding of route-running. (Football has found a new demographic in middle-aged women. You may have heard.) Route-running isn’t just for tight ends with famous girlfriends. “I feel like I can tackle big, big things because I can see the route.” Elena explains how careful planning, studying, and vision allowed her to see her throughline—from life as a partner at Jackson Walker and in-house counsel at USAA, to General Counsel at Massage Heights, and now, to deciding to head up her own bespoke compliance solutions business. She talks about how to accept the hugeness of a task, develop a process, and visualize the product. It’s the type of big-picture vision that separates a good leader from a great one.
Gumbo and Tamales
Elena grew up in San Antonio. She obtained a B.A. in International Studies from Boston College, and a J.D. from the University of Southern California’s Gould School of Law. She teasingly describes her background as “spicy.” On her father’s side, she descends from MexicanAmericans that settled in Eagle Pass. Her mother’s Houston clan is Cajun, from Louisiana. “We were eating gumbo for one holiday, and tamales for another.”
She is hovering around her twentieth year in the practice of law. For several years, Elena served as General Counsel for Massage Heights. Founded in 2004 in San Antonio, what started as a small, familyowned business has grown into a franchiser whose franchisees provide professional massage services across the country. Massage Heights offers membership and loyalty programs, showcasing self-care as an imperative, rather than a luxury.
Elena recently decided to put her business and compliance skills to use under her own banner and stand up a forthcoming compliance solutions company. Under that entity, she aims to offer a wide range of services to help companies do the right thing, mitigate risk, and comply with laws and contractual requirements so that they can focus on revenue and operational growth. With it, she plans to introduce a law firm component, providing general counsel services for businesses needing to outsource this function on a fractional basis. It’s a need she’s very familiar with, having seen franchisees—effectively, small businesses—express a desire for these types of services.
Reasonable Risks
When I marvel at her enthusiastic leap into such a different role, Elena is nonplussed. She tells me that it’s all well thought-out. She has spent decades being what she calls a reasonable risk-taker. Lately, she explains, she has been coaching her young daughter in taking these “reasonable risks.” (Gathering her courage to go zip-lining. Encouraging her daughter to ask a barista for sugar, unaccompanied.) This makes sense: in Elena’s world, big changes are made of a series of small, intentional, and reasonable changes in the direction of where you want to go.
Her explanations are crisp, and it’s clear that Elena has spent time thinking about how she presents in the world. I bring this up, as well as the discipline it must take to think before she speaks and acts. “It’s very intentional,” she agrees. She cites good work by USAA in fostering the further development of her executive leadership skills, as well as a personal coach whom she sought out to confront hard questions about her career trajectory, both of which ultimately led her to her new ventures.
Small Steps in the Direction You Want to Go
Prior to starting her businesses and serving as General Counsel, Elena spent five years at USAA, first as an Attorney for the Life Insurance line of business, and then as the Executive Director of Life Insurance, Annuities, and Health Insurance. Elena arrived at USAA after nearly a decade with Jackson Walker in San Antonio, where she practiced commercial litigation on a big stage, with its characteristic heavy demands. Her attorney position at USAA had her flexing those well-trained muscles—conditioned by many years as a high-stakes litigator—where the best attorneys must deeply understand the client’s business.
While USAA’s business (life insurance) was somewhat unfamiliar and highly regulated, it was not entirely unlike taking on a new, albeit singular, client. Where Big Law can famously thrive on individual personalities, USAA’s hallways are mammoth and hivelike. There is a palpable steadiness, a proud and efficient predictability about its headquarters. Process is key. Developing a process would soon be Elena’s day-to-day, and where she feels as if she’s done some of her best work. When I ask her what she is most proud of among her legal work, she gets up from her seat across from me. She sits down next to me so she can really emphasize what’s important, in close range. She tells me a story of how USAA’s Disciplined Execution (or, “DE,” for those playing inside baseball) came to be, and how she learned to tame a beast of an assignment that seemingly no one wanted, but for which she essentially volunteered.
Soon after Elena arrived at USAA, the enterprise set about to document every law and regulation that touched its many lines of business. Some thought the idea was merely a passing thought and unlikely to come to fruition, while others found the task to be so laborintensive as to make it impractical. Regardless of how improbable or impossible it sounded, Elena dutifully followed the evolution of the project, which soon was no longer just an idea. She explains that she loves to take the ugly thing and make it pretty. To take command and build consensus. It was clear, though, that this task was perhaps the ugliest of ugly things, and it would have been easier to actively avoid it. Owing to her relative newness in the role and lack of in-depth experience with the regulations at issue, it would have been simple for her to demure. She agrees. But she saw the route, and longed to make this ugly thing pretty. In her new venture, she hopes that her clientele will see value in partnering with someone who is adept at finding those throughlines.
A (Rare) Chick with Command
A glance at Elena’s Clifton StrengthsFinder assessment will have you staring at Command, which might explain her deep well of determination in difficult circumstances. Command is rare, and it is the least-prevalent top strength among women (by Gallup’s own metrics). It is so unusual that when a StrengthsFinder coach-turned-podcaster caught wind of Elena’s top-ranking Command, she featured Elena on a podcast (cheekily styled: “Chicks with Command”). The show digs into how this statistical outlier strength manifests in women and offers some insightful tidbits on how to play to this strength.
I looked up “Command.” It might as well read as a description of an effective executive or general counsel:
Once a goal is set, a restlessness sets in until you have aligned others with you. You are not frightened by confrontation; rather, you know that confrontation is the first step toward resolution. Whereas others may avoid facing up to life’s unpleasantness, you feel compelled to present the facts or the truth, no matter how unpleasant it may be. You need things to be clear between people and challenge them to be clear-eyed and honest. You push them to take risks. And while some may resent this, labeling you opinionated, they often willingly hand you the reins.
LEADing the Way
We have been talking about serious things in a not-so-serious place. I hand her a cup of quarters, and we play pinball, to her delight. We keep talking. On her list of things that bring her joy, Elena cites being in the room with young lawyers or students when they realize they are good enough and smart enough. It’s not just a platitude; she’s been working to create opportunities for young lawyers to succeed for some time. She enjoys mentoring others, and speaking opportunities to help companies and organizations develop their teams with practical leadership skills. She spends her free time putting this into practice with her daughter’s Girl Scout troop, and the local women’s bar and its affinity organizations.
In January 2020, the Bexar County Women’s Bar’s LEAD Academy announced that Elena would serve as its next Director. Founded in 2015 by the BCWB’s Officers and Board of Directors— and originally led by Past-President Tiffanie Clausewitz—the LEAD Academy was inspired by the need to help talented women excel in the practice of law. (Among its early accolades was the 2018 Star of Achievement Award presented by the State Bar of Texas.)
In being so intentional in her career, Elena finds real joy in the little things, the unexpected.
LEAD highlighted this first passing of the torch with much fanfare. Soon after, COVID set in. With no guidebook, Elena pivoted a program that has personal (and in-person) connections at its heart. As she had before COVID, she began each virtual meeting of LEAD’s Steering Committee with LEAD’s Mission Statement. There was a cause at stake, and it was dear to everyone involved. What may have been monotonous rang differently. She’d again been entrusted with making the (unexpectedly) ugly thing pretty: ensure that a newer organization to empower women attorneys lived to tell the tale of its two-year-long COVID class. Eight years after selecting its first class, LEAD Academy has not just survived, but indisputably thrived, and has become known state-wide as a model leadership academy for women attorneys.
Finding the Gift in Everything
In being so intentional in her career, Elena finds real joy in the little things, the unexpected. She tells me she loves dancing (the cumbia to hip-hop) and traveling. She is a former gymnast. While she insists that she hates to work out, her commitment to a pretty serious-sounding personal trainer (with a militant-sounding intonation) suggests otherwise. When Elena asks for her trainer’s opinion on the matter, her trainer tells her, indignantly: “You lie. You love it. You push yourself harder every day and you wouldn’t do that if you didn’t love it.” We know the same Elena, this trainer and me.
She gets a little choked up when talking about her daughter and the woman she hopes her daughter will become. She talks about her husband, whom she met in college, whom everyone calls “Sully.” (Few of her friends can recall his actual first name. It’s Chris.)
. . . The next day, Elena texts me a photo. She’s gotten some time to set down the heavy business of life for a bit. It is a photo of her daughter and husband, playing pinball. It brings her joy.
