Six Sales Leaders on Building Careers and Raising Families

Harry Stebbings hosts a 2023 Mother's Day conversation with six sales leaders about careers, family and parental leave. Each participant describes her own circumstances; their advice is personal rather than a single prescription for all parents or workplaces.

Jessica Arnold, then a sales development leader at Amplitude and mother of two, values having an independent life beyond parenting and showing her children that it is possible. Lauren Schwartz, an enterprise sales leader at Fivetran and mother of a young daughter, says motherhood deepened her empathy for working caregivers and their trade-offs.

Stevie Case, then Vanta's chief revenue officer and a single mother of an 18-year-old, says parenting forced her to develop focus and intentionality. Renu Gupta, a sales adviser and mother of two, values showing her children an equal partnership between parents who care about both work and family.

Maggie Hott, who had recently joined OpenAI, says she wants her daughters to see that they can pursue their ambitions. Julie Maresca, then leading global accounts at Atlassian and raising three boys, hopes to encourage women earlier in their careers and normalize both parents working and contributing at home.

Case describes the early years of single parenthood as painful and messy. After moving from product into sales, she traveled for work and became a single mother with full custody. She remembers trying to demonstrate a product while driving her crying daughter to daycare, without the resources to outsource much help.

She learned to concentrate on the task immediately in front of her: work when working, and her daughter when at home. Life later became less complicated, but she retained that focus. She emphasizes that ambitious parents will face hard moments without clean solutions and that her experience is not a universal formula.

Maresca treats balance as an ongoing practice rather than something achieved every day. With a global team she may take an evening call after her children sleep, but protects time for dinner and bedtime. Planning and communicating expectations reduce last-minute decisions and the regret of being distracted wherever she is.

She relies on her husband, friends and neighbors when plans change and chooses activities according to what matters to her. For example, she may skip an after-work group class but make time for individual coffees with colleagues. Her approach reflects the support and choices available in her own life.

Hott's first practical principle is that time is valuable. She recommends asking friends, family, neighbors or a partner for help, and, where affordable, paying for services such as grocery delivery or occasional cleaning. She explicitly recognizes that paid support depends on having the means.

Her second lesson is to let go of perfection. Rather than spending hours making an ideal birthday cake, she might buy one and use that time for reading, dancing or being with her daughters. For her, presence and care matter more than performing every task perfectly.

Schwartz says protecting mental health is difficult and recommends finding an activity that belongs to the parent alone. Singing in a long-standing women's group gives her a creative outlet and replenishes her energy. The group provides remote access to rehearsals when she travels, helping her sustain the commitment.

Arnold describes guilt after becoming a mother: she felt that she could no longer give every part of life 100%. A family practice introduced by her mother—regularly identifying values and goals—helped her notice when guilt arose and ask whether she had actually violated her own standards.

Her practical approach is to write annual goals, identify core values and share them with family and her support network. She says this makes priorities visible, allows them to change and gives others a way to help. It does not eliminate guilt, and she still has good and difficult days.

Asked what a manager can do, Arnold suggests curiosity: ask about school drop-offs, travel, breaks and what a colleague needs. She says leaders do not have to know every parent's experience in advance, but they do need to learn about the people they work with.

Gupta says women, women of color and parents can be underrepresented in sales leadership, leaving her with fewer people who look like her in executive or customer meetings. She sees efficiency and qualification as strengths built through managing limited time, while acknowledging that proving one's capability can require extra effort.

She encourages working parents to find a community, speak openly and seek support. If a person cannot safely disclose a pregnancy or plans to grow a family for fear of losing opportunities, she suggests considering whether the organization is right for them. The panel recognizes that such choices may not be equally easy for everyone.

Arnold recalls feeling pressure to assimilate into mostly male leadership groups and hide parts of herself. As she began sharing more of her life, she found colleagues responded positively. She now views difference as a strength that can help leaders connect with people in different ways.

Schwartz says becoming a mother broadened her attention to colleagues with responsibilities outside work. She mentors people from diverse backgrounds and supports women in enterprise sales. She remembers her mother, an early female vice president at Morgan Stanley, challenging exclusion from meetings held at a men's club; her mother died when Schwartz was nine.

Maresca connects parenting with leadership that combines encouragement and candid feedback. In her view, difficult feedback is easier to hear when people know their manager cares about their success. She values trust and vulnerability in close teams, while the comparison to family is her own leadership perspective.

Asked whether employees can safely admit they are struggling, Maresca sees progress but says workplace culture still matters. She thinks some leaders have earned the space for honest conversations, but organizations must also welcome them. The panel agrees there is further work to do.

Case recalls hiding her single-parent responsibilities early in her sales career and saying yes to every trip or opportunity. She sometimes flew relatives in to care for her daughter without telling colleagues how much coordination was involved. She describes the experience as isolating and painful.

At Twilio, her manager Allison Welch championed her career and, when promoting her, wanted to include her motherhood in the announcement. Case says being seen as a whole person changed how she felt at work. She also recalls mentor Matt Golden teaching her that honest, human connections matter in sales.

Stebbings asks whether vulnerability is a privilege of success. Case agrees that privilege matters but urges leaders who have it to make room for others to be human and make mistakes. She says people may not need to wait for an arbitrary career milestone before allowing themselves to be more open, where it is safe to do so.

Hott says leaders set an example when they speak openly about parenting and difficult days. At eight and a half months pregnant, she saw an enterprise leadership role at Slack and initially assumed she should not apply because she would soon take leave.

Two male leaders encouraged her, emphasizing a long-term investment in the right person rather than the next few months. She applied, interviewed and got the position. Hott says her career might have been different had she ruled herself out, and encourages others not to assume family plans disqualify them.

On parental leave, Hott says time away can create a real career pause if the organization keeps moving without the parent. She advocates more equitable leave for birthing and non-birthing parents, including pay, so caregiving and career costs do not fall disproportionately on one person.

She also discusses postpartum depression and the value of partner support in the early months. Her references to studies and prevalence are not sourced in the interview; the panel's discussion is about support and policy, not a clinical assessment or guarantee of health outcomes.

Stebbings asks whether partners should be required to take leave. Hott supports strong measures to encourage or require it and stresses that people need pay while away. Her comments about US policy are a broad 2023 assessment, not a current or comprehensive account of federal and state rights.

Schwartz says leave policies should cover different family structures, including adoption and same-sex parents. For her own leave, she focused on maintaining momentum by preparing other leaders, setting expectations and creating a plan for the team's decisions and accountability while she was away.

On checking messages during leave, Schwartz says each person should choose what feels right. She set boundaries and limited periods for thinking about work, trusting colleagues to make decisions while she spent time with her newborn. She acknowledges the temptation to stay connected and the work required to establish coverage.

Hott offers a practical sequence for improving leave policy: research comparable employers, gather colleagues and allies, find an executive sponsor, and bring clear requests and evidence to decision makers. She recommends constructive discussion rather than assuming outdated rules were deliberately designed to exclude parents.

Sales compensation adds details that a general policy can miss. Hott suggests agreeing on account coverage, treatment of deals that close during leave and a reasonable quota ramp on return. Her own coverage plan specified when she wanted to be contacted and when she did not; another parent may choose different boundaries.

Schwartz recalls joining Fivetran while pregnant and discovering that the leave policy required nine months of tenure, a threshold she could not meet before her due date. She worked with colleagues to revisit it, framing the issue around the company's inclusion and recruiting goals. Her account of legal protections is specific to her understanding at the time, not current legal advice.

She also urges salespeople to examine how commissions and variable earnings are handled during leave. Depending on a company's resources and deal structure, teams might use shared credit or negotiated splits so coverage works for both colleagues and customers. The panel treats these as policy choices to discuss in advance.

Gupta explains that she often left the sales floor around 4 or 4:30 to pick up her child. A supportive sales leader acknowledged her work and let her leave without making her feel guilty. She had made family commitments visible to colleagues and managers.

She encourages leaders to ask about their team members' non-negotiables, such as a school performance or swimming lesson, and to support them. Employees, too, can communicate boundaries and priorities. The examples come from her circumstances and do not imply everyone has equal control over their schedule.

Schwartz recommends building a personal board of advisers across generations, companies and professions. Her women's circle and the sales leaders on the panel provide places to discuss transitions, challenges and celebrations. She says people must take responsibility for building those relationships.

She recalls being open about pregnancy and family plans when joining her company. A male leader supported her and later spoke publicly about her parental leave in a celebratory way. She emphasizes that men as well as women can be effective mentors and advocates.

Stebbings asks whether simply telling an employee that they can discuss their needs is enough. Schwartz says openness and curiosity are a good start, including for employees caring for older relatives or managing other commitments. The key is making space for different experiences.

A panelist describes mentor Kevin Egan's emphasis on enabling people to work in ways that suit them while remaining accountable for results. She argues flexibility and success can coexist and that leaders should adjust expectations when needed. The point is to remove unnecessary guilt rather than lower the importance of work.

Arnold remembers a senior leader, Thomas Hansen, encouraging her to take her full leave and spend it with her family. The brief conversation made her feel confident and supported. She says leaders may not remember every such moment, but the way they make people feel can last.

Case credits leaders at Twilio, including Welch, with making discussion of family routine: parents openly mentioned pickups, holidays and life events. She says employees early in their careers look for signals that it is safe to share their own circumstances. A leader need not be a parent to offer that signal.

Hott recommends normalizing children and caregiving in work life, including being honest when a child is sick or appears on a call. She also describes pregnancy support channels, conversations with leaders about family journeys and family events as ways to build community. Participation and disclosure should reflect each person's comfort.

Asked about office requirements, Hott says each company will make its own choices, but leaders should preserve flexibility for school events, illness and other family needs. Such commitments can be harder to accommodate in a fully office-based routine, so expectations should make exceptions clear.

In closing advice, Hott encourages confidence and recognizing guilt without letting it define a person. Schwartz urges people to ask for the support and flexibility they need, while Arnold emphasizes discussing career and family expectations with a partner where applicable.

Maresca advises choosing a company and colleagues whose work and culture make the trade-offs meaningful. Case says parents need not apologize for ordinary family commitments. Gupta recommends doing good work and finding a community for career, parenting and life support. Stebbings thanks the panel and closes the conversation.