How These 14 Companies Celebrate The Holidays
We asked startups, Fortune 500s, and remote-reliant teams to share how they keep the holiday spirit alive at work.
Yesterday, we celebrated our third annual Secret Snowflake at PowerToFly! We wanted to know what other companies do to keep the holiday spirit alive at work, so we asked our partner companies to share one or two of things they do to celebrate. From spending quality time together in person (even when their teams are spread across multiple locations!) and giving back to their communities, to taking time to rest and recover for the new year (a couple of them even shut down between Christmas and New Years), their answers did not disappoint.
Read on to get an inside look at the many creative ways these companies celebrate the holiday season and kick off the new year!
Greenhouse — A New York City New Year.
Greenhouse SF Party
"At Greenhouse, we like to end the year on a high note and start the new year off right. To close out the year and celebrate our successes, each of our office hubs hosts their own holiday party and our distributed employees are given the opportunity to choose their own Greenhouse-sponsored activity. We love seeing each employee show their own personality through the photos that are posted on Slack the next day. As a distributed workforce with teammates all over the United States and Dublin, we don't always get to meet face to face. So, we like to ring in the new year together by bringing the entire Greenhouse family to our headquarters in New York City for Kickoff Week. During this week, we get to meet our fellow teammates in person, show off our unique knowledge at Trivia and karaoke night, and bond on both a company and team level."
[Learn more about Greenhouse.]
Quip — Cookies and camaraderie.
"This year, Quip held our fifth annual Holiday Cookie Cook-off. Quip employees brought in cookies to share with their coworkers and compete in categories including Most Millennial Cookie, Best Non-Cookie Cookie, and Grand Champion Cookie. More important than the baking and the voting, everyone at the company looks forward to eating all of the amazing cookies, and socializing with coworkers across the company."
[Learn more about Quip.]
Blockstack — White elephant and wacky socks.
"At Blockstack, we held a 'Fuzzy Socks White Elephant End of the Year Party' this year for both HQ and remote team members. We provide the fuzzy and patterned socks so that everyone who joined (team member and their families/partners) can wear them and feel included as part of the celebration, whether in person or remote. We played White Elephant with gifts provided by the company, so that we can swap gifts around. For remote folks, we ran a spreadsheet with fun descriptions of the gifts to intrigue remote folks to choose the present."
[Learn more about Blockstack.]
Braintree — Letters to Santa.
"At Braintree, every year we look forward to participating in Chicago Sun Times' Letters to Santa program. Every child deserves to get gifts for the holidays, so this is our chance to help make that a reality. We receive letters from local elementary schools, and Treeps sign up to help purchase gifts between $25-$30, ensuring every child has a happy holiday! This year we saw participation from over 180 employees, who provided nearly 350 gifts for local students."
[Learn more about Braintree.]
Dell — Random acts of kindness.
"At Dell, we close for the week of Christmas to give everyone time to relax and recharge before the new year. We also keep the holiday spirit alive through different team activities. This year, one of our teams is having an acts of kindness contest. Participants contributed $10-$20. Now they have until January 3rd to complete ten acts of kindness (e.g. giving up a parking space at the mall, or your place on line at the cashier, or any other). At the end, each participant will submit their top act of kindness and the team will vote on the #1 act. The winner gets to select the cause that the entry money is donated to."
[Learn more about Dell.]
T. Rowe Price — A "Holiday Giving Campaign."
"T. Rowe Price hosts an annual Holiday Giving Campaign, and every year, associates go above and beyond to make an impact. More than a dozen nonprofits around the world are supported each year by the firm's 7,000 associates. Giving and serving in the community are important aspects of T. Rowe Price's culture, and the Holiday Giving Campaign is a longstanding tradition that has grown along with the firm. Through donations and volunteerism, T. Rowe Price's associates make a difference in their local communities all year long—but the holiday season especially sparks a spirit of generosity and camaraderie. To learn more about T. Rowe Price's culture of giving read out latest report at, TRowePrice.com/CRReport."
[Learn more about T. Rowe Price.]
CarGurus — A top-secret, surprise private performance.
"Among many holiday traditions at CarGurus, such as donation drives, individual team celebrations, and Secret Snowflakes, we like to celebrate the start of the new year with a company-wide party! Last year we invited all 900 employees, along with a plus one, to the House of Blues, for a private surprise performance by Snoop Dogg! This year, we will keep up with our tradition by having our subsidiary company PistonHeads join us to partake in the holiday festivities. The live performance is still under wraps, but we cannot wait to share who it is. Follow us on our Instagram culture page, @cargurusculture, to see all of the fun that is about to come during the rest of the holiday season!"
[Learn more about CarGurus.]
Procore — A "Week of Giving."
"Towards the end of the year, each Procore office gets to celebrate, reflect, and give back in ways that are unique and special to our offices. But celebrating isn't all we do—our Austin office, for example, participates in a "Week of Giving" where we give back to the local community through donation drives, volunteering at local charities, and writing gratitude cards for children at SAFE, a human service agency in Austin serving the survivors of child abuse."
[Learn more about Procore.]
Vrbo — Unique themed parties + festive sweaters!
Vrbo's 2019 Haunted Holiday Soiree that was on Friday the 13th!
"Each Vrbo office around the globe is uniquely decorated and has its own holiday celebrations, but our One Team value is what brings us all together to reflect back on the year we've accomplished together. We gather in our most festive sweaters for a holiday version of our monthly companywide meeting with leadership, 'Table Talks,' to recognize achievements and discuss what we can look forward to in the new year. In Austin, we hosted the Latinos in Tech End-of Year Fiesta, which brought together 10+ tech companies to celebrate the city's strong and growing Latinos in Tech community. An Austin employee favorite is our holiday party that we've hosted Downtown at Moody Theatre for the past three years!"
[Learn more about Vrbo.]
VideoAmp — Contributing to the community.
"At VideoAmp, we celebrate the holidays and get into the Holiday Spirit by giving back! A few years ago, VideoAmp was a tiny company with roughly 17 employees, and one thing we all shared together was a commitment to people. "VideoAmp Gives Back" started off simple. At first, we worked with organizations that allowed us to volunteer, like the Salvation Army. Eventually decided to do everything in house during the holiday season: from lunch kits, hygiene products, and toy drives to sponsoring families' Christmases. All these events were recommendations from our employees, and as our company grew bigger (we went from 70ish in 2018 to over 200 employees in 2019), so did VideoAmp Gives Back!"
[Learn more about VideoAmp.]
Scout RFP — A sophisticated San Francisco soirée.
"To celebrate the holiday season, Scout RFP hosts a Holiday Party every year at a venue in San Francisco, where we are headquartered. Our employees who are remote or work in another office fly in, and everyone is invited to bring a plus one. We rent out a private section of the venue and have food and drink available to all our guests. It's so fun to see all of our coworkers outside of a work setting, dressed in cocktail attire, and with their plus ones."
[Learn more about Scout RFP.]
Intuit — A holiday market in support of small businesses.
Every December, Intuit puts on a Holiday Small Business Market, where local businesses and vendors are invited to Intuit campuses to showcase their creations and (hopefully) spark unique and creative gift ideas for Intuit employees. The event encourages support of local businesses, a sentiment in line with Intuit's mission of powering prosperity. Many of the local vendors are also small business customers of Intuit's QuickBooks product. Intuit also has a Toys for Tots drive in partnership with the Marine Corps and our team at Intuit Boise also partnered with the Make-a-Wish Foundation to write letters from Santa. For every letter written, Macy's will donate $2 to the Make-a-Wish Foundation. The team hand-wrote 378 letters!
[Learn more about Intuit.]
SeatGeek — Giving, giving, giving.
"Here at SeatGeek, the holidays are all about giving. We have an employee-run group internally called GiveGeek that organizes charitable events and donation opportunities for the company. This holiday season, GiveGeek has partnered with a few different organizations to create 3 unique opportunities for employees to give back to the community. From purchasing gifts for under-resourced children, to writing cards for local seniors and partnering with a local food drive, GiveGeek helps create opportunities for SeatGeek employees to make a positive difference in the community."
[Learn more about SeatGeek.]
Nextdoor — An end-of-year shutdown.
"At Nextdoor, we're scaling quickly and have offices/team members in over 10 locations around the world. In addition to some amazing Holiday parties, we're grateful to have been given the opportunity to implement an end-of-year shutdown and our offices will be closed until the first day back in the office on January 2nd. This allows our team members an opportunity to step away from all of the hard work we've put in at Nextdoor and reconnect with our community of friends and family."
[Learn more about Nextdoor.]
January is National Mentorship Month— the perfect time to focus on growing and building important relationships with mentors that will positively affect your professional career.
Research shows that mentorship greatly improves career outcomes by providing professional guidance, skill development, and support through major work and life transitions.
We asked some of our partner companies to tell us about the mentorship opportunities they offer. If you’re ready to unleash your full potential by joining an impactful mentoring program, keep reading to hear what they said. (Plus, they’re all hiring—check out their open jobs under each entry!)
“Clarus Commerce has been running a mentorship program for the last 9 years. Here is how it works:
- Senior leaders nominate mentors within their department.
- The program lasts for about 6 months.
- Those who are interested in being mentored provide 6 topics that they’d like to discuss in mentoring meetings, which help us pair people up. Mentoring topics should focus on topics such as: leadership, how to manage up, presentation skills, communication, work life balance, etc.
- We leverage our Insights and Discovery profiles that each employee has to help better understand each other’s communication styles and help facilitate great discussions.”
Learn more about Clarus Commerce here.
“PwC professionals are provided learning opportunities, supportive career growth and unique mentoring opportunities to help them to fulfill their potential. The firm has several programs that include intentional mentorship and focus on building representation, inclusion and development of their people. For example, the firm launched Enrich, an experience designed to support the development and leadership skills of high-potential female and racially and ethnically diverse senior managers and directors. There is also Thrive, an innovative two-year experience for Black and Latinx entry-level new joiners that helps lay the foundation for a successful career through culture workshops, networking, connectivity and leadership engagement.”
Learn more about PwC here.
“At CallRail we have a program called Connection Point where individual contributors are paired with members of the Senior Leadership Team. Each pair is together for a full quarter and are given topics for their meetings, topics range from; career stories, situational advice and feedback, etc. At the conclusion of the quarter the individual contributors that have been in the program have a round table lunch with the CEO. This has been a great way to foster deeper connections within the organization, demystify senior leadership and help individuals see a path forward.”
Learn more about CallRail here.
“Automattic’s Design Mentoring program is a mutually beneficial partnership providing development opportunities for all. Mentees pick up new skills or get guidance with a project. Mentors practice communication, leadership, and knowledge sharing. The organization benefits from more engaged, productive employees, who have increased job satisfaction because mentorship encourages meaningful work that aligns personal and professional goals. In our distributed work environment, mentoring provides a human connection and a trusted space to grow. Tapping into all of the design experience and skill that our organization has is a powerful way to grow individually … and collectively."
Learn more about Automattic here.
“Relativity Women of the Workplace (RelWoW) Mentorship Circles is a group mentoring program that brings together women at varying stages in their careers and from every department at Relativity. The program sessions are curated by our team and include materials, talking points and action items to help create open dialogue, build connections and develop skills for personal and professional development. The program runs around six months, and includes a kickoff, mid-point event exclusive to program members, and a closing celebration. Relativity also plans to pilot a new mentoring program with broader reach across the company in 2022.”
—Yvonne Frazier – Executive Assistant
Learn more about Relativity here.
“CDW Business Resource Groups are a key source for networking and mentoring opportunities. In 2019, our BeU BRG launched a formal mentoring program through their Project IMPACT initiative aimed at recruiting, retaining and promoting Black coworkers. It has been a successful program that has brought coworkers together across departments and roles, sharing new experiences and perspectives for both mentors and mentees.”
Learn more about CDW here.
“BRIDGE is Kinesso's reverse mentoring program bringing together senior leaders and future leaders globally. Our program pairs employees with Kinesso's Senior Leadership Team, but rather than leadership mentoring employees, our employees mentor our senior leaders!
Through mentorship programs like Bridge, Kinesso's brings together employees across generations, cultures, territories, and job levels. Giving our future leaders the opportunity to share fresh perspectives and innovative ideas allows our current leaders to look at inclusion, capabilities, collaboration, and connectivity from a completely different lens.
"(Bridge) is immensely important for many reasons, but most of all, it shows that no matter where you are in your career, you should never stop learning and growing."
—Arun Kumar, CEO at Kinesso and Global Chief Data & Marketing Technology Officer at IPG”
For more information on Kinesso, please visit Kinesso.com/careers.
Learn more about Kinesso here.
"At SoundCloud, one of our core behaviors is to embrace the challenge- but that doesn’t mean that you go at it alone. We encourage SoundClouders to ask for help and to give help to those who it need along the way. Over the past few years we have offered a mentorship program that connects rising SoundClouders with under-represented identities (gender/race/ethnicity) with more senior level employees around topics of professional branding and career growth, influencing and emotional intelligence, and strategic thinking. In 2022, we aim to launch 2 cohorts of mentorship/coaching targeting different ranks of women of color."
Learn more about SoundCloud here.
“BlackRock has nine employee networks and four professional networks – all of which offer mentorship programs or opportunities.
Our employee networks: Mosaic; Ability & Allies Network; Asian, Middle Eastern & Allies Professional Network; Black Professionals & Allies Network; Families & Allies Network; Out & Allies Network; SOMOS Latinx & Allies Network; and Women's Initiative & Allies Network.
Our professional networks: Analyst Alley, Associates Arena, Global Administrative Initiative Network, and VP Village.”
Learn more about BlackRock here.
“Having both formal and informal mentors is crucial to elevate any career. At Lockheed Martin, mentoring is the development of meaningful relationships to transfer valuable knowledge and understanding from one person to another. It is a personal enhancement strategy through which one person willingly facilitates the development of another by sharing known resources, expertise, values, skills, perspectives, attitudes, and proficiencies. Our mentoring program is tailored to the individual employee to give them the right tools, the right resources, at the right time.”
Learn more about Lockheed Martin here.
“Autodesk is a place where you can shape your future and help others do the same. The Autodesk Mentorship Program empowers employees to take ownership of their careers and build on a mindset of learning from each other by offering mentorship opportunities for professional and personal development, peer-to-peer learning, and focused networking. The program helps you identify your goals and recommends matches for a mentor or mentee to help you accomplish them. Through the Autodesk Mentorship Program, employees can make connections, grow their skills, explore opportunities and build their career paths.”
Learn more about Autodesk here.
“Cummins Women’s Empowerment Network (WEN) focuses on a mission to create the right environment by advocating for equal representation, empowering women, and fostering inclusion for every employee in all work assignments at all levels.
As part of the work to achieve such a mission, WEN focuses on mentoring and development initiatives designed to foster mentoring relationships, broaden employee networks, and provide opportunities for personal and professional growth. Initiatives include Speed Mentoring Sessions, Personal Development & Networking Events and WEN Mentoring Circles Program. This annual Mentoring Circles Program provides a monthly opportunity for exempt employees to participate in a forum for open discussion, explore new perspectives and learn from peers and leaders.
Within the Europe region we also have the Cummins Business Services mentoring program which is open to all employees at all levels.”
Learn more about Cummins here.
“Meet a pairing in Millennium’s Mentorship Program: Cari Smalley, Co-Head HR Business Partners, Americas, and Jasmin Zirino, Operations Specialist. They say, "The mentorship program is a fantastic experience for anyone who wishes to join. It allows you to meet someone you do not directly work with and grow your network. It is invaluable to have the ability to work through solutions to problems, use one another as sounding boards, and occasionally just blow off steam in a supportive space."”
Learn more about Millennium Management here.
“Mentorship is about stepping out of our comfort zone, taking charge and acting upon our ambitions, opening doors for others and learning more about the skills that make our own success.
Expedia Group has a volunteer-led program allowing every employee to have an equal chance to grow and succeed. The program has brought together a group of 1,700 Expedians from all over the world who believe in skills development and the power to elevate others while creating Inclusion at Expedia Group. Through a self-service marketplace platform and organized meetup sessions, EG’s Mentoring Program enables all employees to ask for help and embrace their own identity while belonging to a community that thrives through diversity.”
Learn more about Expedia Group here.
“At Equinix, our employee connection networks (EECNs) play an important role in bringing together communities for learning and growth opportunities, including mentoring. While mentees gain much from mentors, we often find that mentors also discover growth opportunities.
By asking these questions, we instill best practices for a successful mentorship:
What does each party want from this experience? How often to meet? Confidentiality: What’s shareable and what isn’t?
Feedback: What are the expectations around giving and receiving feedback?
And remember, a mentoring relationship is like any other relationship—it takes time to develop. Build trust by getting to know one another.”
Learn more about Equinix here.
"At Unstoppable, it is our commitment to having a crypto forward culture. Every new team member is matched with a Crypto Buddy who acts as their first point of contact outside of their direct team, guides them down the crypto rabbit hole, and welcomes them into Unstoppable’s culture. As a fully remote company, making cross-team collaboration a key part of onboarding strengthens our community. This is also an opportunity for the buddy to hone their mentoring and teaching skills. When the new hire has been with the company for six months, they will then become a mentor themselves, driving a continuous cycle of mentorship."
Learn more about Unstoppable Domains here.
“Mentoring@Uber connects employees who are passionate about helping and up-skilling others with those who are seeking guidance and development. It is a way of connecting and sharing challenges on a mutual and reliable relationship —and trying to get another perspective from an unbiased source. It’s also an opportunity to learn from the experiences of others, or collaborate together to come up with a solution to professional problems that arise. People with mentors perform better, advance in their careers faster, and even maintain more work-life balance. And mentors benefit, too.”
Learn more about Uber here.
“MongoDB has offered two pilot mentorship programs to support underrepresented groups. One program focused on promising first-line managers and ICs from underrepresented groups and the other focused on providing executive mentorship to women & nonbinary leaders at the director level and up. In both programs, participants were matched with a mentor with who they regularly met to discuss career planning and personal development. Feedback from both pilots was hugely positive with participants indicating that they received helpful support from their mentors. Members from our ERGs have also served as mentors to our summer class of interns.”
Learn more about MongoDB here.
“Our Black and Latinx ERG, Array, offers a mentorship program pairing individual contributors within Array to C-Suite and VP level mentors, including PagerDuty CEO Jennifer Tejada. Dedicated to leveling the playing field for Black and Latinx employees, the program is structured so everyone can learn from each other. Mentees are paired with mentors from within or outside their department for a nine-month term, which includes check-ins, themed discussions, and monthly one-on-ones. Bri Solorzano, an Array mentee, explained that this mentorship program allows her to build bonds with higher level executives, and share her personal experiences as a Latinx employee and individual contributor at PagerDuty.”
Learn more about PagerDuty here.
T. Rowe Price
“Due to the highly collaborative culture at T. Rowe Price, the firm understands the value of relationships and the opportunities strong mentorship can provide. It is committed to not only developing talent within its walls but developing the next generation of talent within communities.
The firm will launch a new global mentorship program in 2022, which will offer associates the opportunity to connect with colleagues, agnostic of location or business unit. T. Rowe Price also provides leadership development to youth in the community through strategic partnerships such as the Baltimore Ravens Leadership Institute, a program aimed at high school students.”
Learn more about T. Rowe Price here.
“At Pluralsight, we take growth seriously. Which is why we offer a six-month long mentorship program for all of our employees. Our mentorship program is facilitated bi-annually by Women@Pluralsight, one of our Employee Resource Groups (ERGs) and aims to empower participants to recognize their full potential. We intentionally pair mentors and mentees to create connections that encourage the development of skills crucial to success, and foster personal and professional growth. In our most recent cycle we paired nearly 200 participants and have plans to continue growing that number. Because at Pluralsight, your growth is our growth, and vice versa.”
Learn more about Pluralsight here.
“At Yelp, we value and actively foster an environment focused on learning and development. There are a variety of mentorship opportunities available, such as:
- New Hire Mentors — new employees are paired with a team mentor to help them onboard and get settled in.
- Engineering Mentorship Program — any IC engineer can sign up to become or get a mentor within Yelp Engineering.
- Manager Mentorship Program — new engineering managers or proto-managers can get support from experienced managers at Yelp.
- Awesome Women in Engineering — This employee resource group’s mentorship program helps AWE members find mentors or mentee within the group.”
Learn more about Yelp here.
“At Turo, we help each other. We collaborate. We challenge each other. And we create the tools to succeed independently and as a team.
When you join Turo engineering, you’re assigned a mentor, a reliable, single point-of-contact to help you set up your environment, navigate the codebase, and acclimate to Turo’s culture and workplace. Mentors have a great responsibility to ensure new Turists feel welcome, offer encouragement, and provide advice and guidance on complex matters of systems and architecture. Engineers who demonstrate our core values of efficiency, pioneering, and being down-to-earth and supportive have an opportunity to mentor new engineers. Mentoring engineers is a great way to build the skills necessary to further your career at Turo.”
“Mentoring has allowed me to deepen my technical understanding and team connections.”
– Lauren Kroner, Senior Software Engineer
Learn more about Turo here.
“In the US, Moody’s has an intergenerational mentoring program, our Pride BRG members coach youth in the Queer Coders program. Our Women’s, Veterans, and Multicultural BRGs have a variety of mentoring programs, including summer intern mentorship, our Asian Leadership Initiative and our ConectaMos Hispanic/Latinx 1:1 mentoring program. Our Women’s Group Mentoring Program just celebrated its 10th anniversary with over 800 mentor-mentee participants over 10 years. In EMEA, Moody’s offers Power to Act reverse mentoring, mentoring through the Women’s and Pride BRGs, and a parental leave mentoring scheme. In APAC, Moody’s has various cross-BRG and cross-department mentoring programs.”
Learn more about Moody’s here.
“At Condé Nast, we are focused on providing positive career development opportunities. We recently launched a Global Mentorship Program as an option for employees to connect and learn from one another. For six months, employees participate as a mentor and/or mentee to develop their careers, grow their skills and guide one another. The structured framework creates and sustains an inclusive experience that empowers everyone’s growth.
The MentorcliQ platform we use lets us create mentoring pairs based on their interests, experiences and personality compatibility. To date we have had 473 active mentorship pairs.”
Learn more about Condé Nast here.
“Thornburg Small Group Mentor Program was created to bring employees of various tenures and experience levels together in order to cultivate organic relationships and opportunities for influence in a low-pressure environment.
The program consists of six small groups comprised of one mentor and three to six mentees. These groups meet for one hour every month for six months. The series concludes with a virtual event where all participants from every group can meet and share takeaways from their experiences.
- Small group format (not one-on-one)
- Low cost, low maintenance, light structure
- Flexibility for mentors to lead through individual style"
Learn more about Thornburg here.
“Women@Okta’s upcoming mentorship program:
W@Okta’s vision for the year is to empower, develop and support women-identified employees in order to ultimately improve gender diversity at Okta. One of our key methods is to empower the next generation of female leadership by providing a platform for women to connect and learn from one another through group and 1:1 mentorship opportunities. Our Professional Development branch is launching a pilot mentorship program with an initial cohort of 32 mentors and mentees.
Goals: Career, personal and organizational
Share your needs, desires, goals, and challenges; career choice and mobility.
Explore people, resources, information, expertise you need – but don’t have – to speed up, enhance, and ensure your results.”
—Professional Development Lead Christina Ghallagher (Senior Sales Development Representative) & Partnerships Co-Lead Sarah Schiff (Senior Manager, Customer First Recruiting)
Learn more about Okta here.
Karen Klein wrote her first contract when she was 11.
It laid out how much allowance she would earn for completing certain chores each week. When she got her parents to sign it, she told them that she was going to be a lawyer when she grew up.
A decade and a half later, her mom brought out that piece of paper again—this time as a gift for Karen’s law school graduation.
Since then, Karen has written and reviewed a lot more contracts, as well as merger and acquisition deals, IPOs, and internal documents responding to regulatory bodies, including as the current Chief Legal Officer at global legal and compliance technology company Relativity.
While she set out on the path to be a lawyer of her own volition—“I was really good at arguing, and it got me into a lot of trouble at school, so maybe that’s where it came from!” she says, smiling—her career hasn’t been entirely self-directed. Karen attributes a lot of her success to having people believe in her and invest in her career, and we sat down with her to hear more about how she found those mentors and how she pays back their guidance by being a mentor herself.
In-House and On a Team
After finishing law school, Karen started her career at a law firm. That’s where she found her first mentor in one of the partners she worked for.
“I spent 90% of my time working for him, and he was a mentor before I even knew what a mentor was,” she says. “He not only assigned me great work, but he took the extra time to put things in context. After a meeting or a call, he’d sit and talk with me about what had happened, why the client asked the things that they did, why they were concerned, and ask for my perspective.”
Karen credits that mentor with helping her level up from being a person who executes well on tasks to being a person who understands strategically what needs to be done and why it matters. That knowledge set her up well for her next career step.
Even before joining the firm, Karen knew she’d one day like to move in-house. A self-proclaimed “deal junkie,” her favorite projects were ones that had her learn a lot about a client and their business in order to prepare a deal for them. “But then you wouldn’t hear from the client till the next deal, and I was like, ‘Well, I learned all about their business—I want to apply those things now,’” she says.
Being in-house would also let Karen fulfill what she describes as an inherited drive to build a business. “My parents owned and ran a construction company, and it stuck with me. I saw the stress that owning your own business created, but that mentality of building something and being part of something spoke to me,” she says. “The pride in helping to build something, that was enduring, and influenced me in ways I didn’t appreciate at the time.”
So when Larry—who was in-house counsel at a Chicago-based tech company, her then-firm’s largest client—called Karen and asked her if she’d like to join him there, she immediately said yes, though she did tell him that she knew little to nothing about technology.
“‘That’s okay,’” Karen remembers him saying. “‘You’re smart, you understand contracts and liability. We can teach you the tech part.’”
And teach her he did. That first move led to Karen spending 17 years in travel tech, including at places like Orbitz, Kayak, HotelTonight. Other general counsel she worked with became additional mentors, helping her come up the curve on regulatory issues and how to build a team.
A Full Circle Moment
When Relativity came calling, Karen had joined Ticketmaster only a year before, and was planning to stay there for the remainder of her career. It was pre-pandemic, and she was happy with the challenges and the teams she was building. She took a meeting with Relativity’s CEO just to get to know him as someone influential in the Chicago tech community that Karen so valued, and that was the beginning of her new job at Relativity.
“Once you meet Mike, you want to work with Mike,” says Karen, laughing. “It had this pull of nostalgia, that I could round out my career coming back to a Chicago software company, which is how I started out in-house. There were all these exciting things in store for the company, and it seemed right.”
Karen’s actual transition took a little longer—the pandemic had started, and she didn’t want to leave her team in its first few chaotic months—but she officially joined Relativity a year and a half ago, and now serves as its Chief Legal Officer and Corporate Secretary.
3 Lessons and 4 Tips for Mentorship
Reflecting on her career, Karen says she’s learned three main lessons from all the mentors that have guided her:
- How to embrace feedback. “I have some rough edges, and I had a CEO say to me once, ‘You know, Karen, you’re really effective, but you could be even more effective if…’” she says. “And that made me feel inspired to actually do better.”
- How to get outside of her comfort zone. Multiple mentors have told Karen she was ready to learn something new long before she knew that herself. “It was inspiring to me that he was willing to invite me along,” she says of one general counsel she worked for who gave her the opportunity to sit second chair while he navigated antitrust issues for the company.
- How to have faith in herself. “Everyone has to do something for the first time at some point,” says Karen of her fear of making the leap to senior positions like General Counsel and Chief Legal Officer. “Having people who put that faith and trust in me really helped me make leaps in my career I wouldn’t have otherwise been able to make.”
Though she’s now reached an apex in her career, Karen isn’t above seeking out new mentors—including her peers, like other executives at Relativity—and is certainly excited about being able to pay forward all that she’s learned. Her top tips for making the most of a mentorship relationship include:
- Build relationships everywhere. Finding mentors is all about having a connection with people, says Karen. “Trust lets you be comfortable reaching out and asking for that bit of advice, or to bounce ideas off of someone,” she says. “Whether you jump on the phone, or Slack someone, you want a connection that isn’t 100% about the transactional aspects of the work.”
- Agree on the goal. “Establish upfront what you both want from the relationship. What are you seeking from it? What will be in it for them?” she says. “Sometimes people are looking for a place to vent, but that’s not really mentorship.”
- Treat mentorship like a project. That means come prepared with agendas for every meeting, advises Karen. “I’m a list person, so I’ve written down lists of things I wanted some feedback on, or questions I had,” she says. “Of course, leave time for relationship building, to talk about how someone’s life is going. But have specific things that you’re hoping to get out of even a more casual conversation.”
- Circle back and share successes. “One of the biggest satisfactions mentors get is seeing career progressions,” says Karen. “When you make the next step or leap in your career, or something good happens, have a conversation with your mentor to say, ‘Hey, I really appreciate the time you spent with me; here’s what came of it.’ It gives your mentor their own career satisfaction and continual feedback we all want and need.”
As a kid, Maleni Palacios had a long list of questions that no one could answer for her.
“I started asking myself, ‘Why are some countries rich? Why are some of them “poor”? What is this notion of a country and a nation-state? Why do people have different lines of work? Who chooses that for them?’” remembers the associate consultant.
Now, several years later, Maleni works at Capco, where she makes a living out of questioning the world, particularly what the future of financial services will look like. She’s learned that some of the best answers to the hardest questions come when you work towards them together.
We sat down with Maleni to talk about her journey into financial consulting, how she found a sense of community through Women@Capco and Latinx@Capco, two of the firm’s affinity groups, and what she’s most looking forward to next.
Chasing Tangible Change
Maleni grew up in Atlanta, but regularly spent time in Mexico, her ancestral home. She credits the experience of traveling between two cultures as what inspired her to start questioning the world.
“My dad and uncles were constantly talking about the world and globalization, like the implications of NAFTA on trade and migration,” she said. “I was an only child for a long time, in this environment of adults, and found it very intriguing. That’s where my insatiable curiosity was cultivated.”
For this reason, when she moved to New York City to study at Barnard, Maleni was drawn to economics. “A lot of the theories we know about were made by people a long time ago,” she says. “Adam Smith was not here at the turn of the 21st century.”
She also liked how interdisciplinary and direct economics was, especially compared to behavioral and philosophical fields like anthropology and art, which interested her but didn’t seem to come with immediate tangible change for societies. “A lot of what I'm passionate about or a lot of what inspires me is changing people's lives on a daily basis,” she says. “Economic policy directly affects people’s day-to-day lives, and to me, that’s valuable.”
Maleni studied the 2008 financial crisis in college, and wanted to be able to work towards improving the financial system so that things like that didn’t happen again. “I wanted to understand how institutions were regulating themselves, how they use their freedom,” she says. “I liked that at Capco I’d have some specialization, but work with different banks at different scales in different engagements. That was really compelling to me, and why I came here.”
Learning in Community
In her first weeks at Capco, Maleni and her fellow colleagues gave a presentation on demographic shifts as a driver for change poised to impact the financial services industry—and now, just over a year later, she’s used the initial research to publish an official Capco whitepaper titled “Unbanked & Underserved: Latinx Demographic Changes & Creating Financial Inclusion.”
“You can run with your ideas at Capco, and they’ll help you accomplish them,” says Maleni, who adds that she’s enjoying pursuing some of her academic interests at work and positioning herself as a thought leader.
As she networked and collaborated with colleagues at the firm in order to publish the paper, she was reminded of the kinds of discussions she’d been able to have in college, and the community spaces where she felt comfortable having them.
Maleni knew she wanted to continue to find opportunities for those kinds of conversations at Capco, so she joined Women@Capco where she leads Table Talks, a Women@Capco initiative that convenes the women of Capco and allies to discuss intersectional gender-based issues in a corporate environment. She also helped found Latinx@Capco, where she serves as Community Outreach Lead, when interest around it swelled earlier this year.
In both groups, Maleni enjoys getting to know people who share her identities in a space where they can support each other.
“You can talk about best practices that got you where you are: ‘How did you do that, who did you talk to, how did that happen?’” says Maleni. “You get a lot of connectivity, and a support group that can help you through when times are difficult.”
“As someone who’s Latinx, a woman of color, a first gen college student—all of these labels I hold mean that certain environments and institutions were not made for people like me,” she says. “That’s why it’s so important to convene people that look like you when you're at these institutions so that you can visualize a future that includes you.”
Building Impact Together
Maleni says she loves that despite being relatively early in her career, she’s been able to leverage her writing and her community involvement to forge relationships with senior leaders and push herself. That’s been especially true thanks to remote work, she notes, which has let her connect with Capco coworkers all around the country.
When she thinks about what’s next, she knows she wants to keep chasing answers alongside her community:
“I think about where we can have the most impact. Sometimes it’s well-defined and small, like our 20, 30 Latinx@Capco members. Maybe you’re impacting a client at a big Tier-I global bank,” she says. “As people, we get sucked into this idea of ‘we have to be changing the world.’ But sometimes that takes time. Defining where and how you can have the most impact is critical.”
From PR to Finance: How Invesco’s Rona Gilbert Stretched Her Comfort Zone to Grow Her Career (And How You Can, Too!)
Rona Gilbert isn’t a numbers person.
But that hasn’t stopped her from becoming a Senior Vice President and Divisional Sales Director at retail investment firm Invesco.
“I get data and spreadsheets given to me, but I’m a people person, a strategy person. You don’t have to be an analyst. I’m just one example of someone who's been able to make [a career in finance] work,” says Rona.
And that’s especially important for other women to realize, says Rona. There’s no one-size-fits-all version of what a successful career in finance looks like, and the field needs more diversity of all types, including gender.
“Financial advisors have a lot of female clients, but women aren’t represented, so the end users of our products aren’t as broadly represented as they need to be. More women need to get into these roles,” she adds.
And she’s a perfect example of just how to do that.
We sat down with Rona and asked her about how she began her career in PR and communications and transitioned into financial sales—and what she learned along the way that she’s excited to pass on to our readers.
“In some fields, there's a perception that you need to have a certain pedigree, either where you went to school or what you studied,” says Rona. “I didn’t have that. I’ve been a generalist.”
Rona started her career in government, working as a legislative aide for a state senator. She didn’t have the political science degree most of her peers had—she’d studied communications—but she knew that there’d be a public relations component to the job, and that she’d do well there.
“I didn’t have the government degree, but I didn’t let that deter me from applying for the job,” says Rona. She got it, and spent several years in government before transitioning into doing public affairs and government relations at a consulting firm in her home state of Ohio.
When it came time to leave the Midwest for a different climate, she got a job at a financial firm doing in-house corporate communications. It built on her experience, but she quickly realized it wasn’t the ideal job for her.
So she raised her hand and volunteered to do some presenting on behalf of the sales team. Their then-presenters were both men, and they appreciated the opportunity to add a woman to the bench. She traveled around the country for a year, giving keynote addresses at conferences and other events, in addition to doing her main role, until eventually she was offered a full-time role on the sales team.
With that exposure to the sales team, she ended up moving into a salesperson role when it came available. Once again, she’d skirted the normal path—internal sales consultant to external salesperson—by stepping outside of her comfort zone and going for the opportunities she wanted.
She stayed at that firm for 12 years, until she heard about an opportunity at Invesco via a friend. The chance to head up the west coast sales team felt like the perfect next step, so she went for it.
Now she’s in her first people management role in finance, with 11 salespeople reporting into her, and working to help them build their careers and find success—including by stepping out of their comfort zones.
1) Look for a mission that excites you. While she enjoyed her time in PR, Rona says she’s much more motivated by the real-life implications of the work that Invesco does. “The role financial advisors play for their clients is in helping people achieve their retirement goals, helping them save enough and invest enough to where they can send their kids to college,” she says. “It’s about what people are trying to do with their lives and having enough money to pay healthcare bills and very real things that everybody deals with. And it's easy to relate to our end clients because I'm in the same boat.”
2) Find a guide. “Whenever I stepped into a role that I was a bit over my head in, I always found a colleague or a person that I could connect with and who could help me learn the ropes,” says Rona. “Aligning yourself with somebody that you trust can help get you over the hurdles. Every job I’ve ever had, I always had at least one of those.” She suggests starting with someone who’s achieved what you hope to achieve and aligning yourself with them by asking for their feedback.
3) Think about risk mitigation: what’s the worst that can happen? Moving into a sales role (and a commission-based compensation structure versus a salaried one) for the first time required Rona to take on a lot of risk, but she felt confident that she’d be okay even in the worst-case scenario. “It goes back to my strategic planning days when I was a communications consultant,” she says. For example, a salesperson considering taking on a new job in a different territory might have to think about their family. Would their kids not acclimating well at school be the worst thing? Is that a deal breaker or not? “And also ask what the best thing that could happen is. If you’re comfortable with those parameters, hopefully it’s the best that happens,” she says.
4) Remember your past accomplishments. Doing something new is scary, and it can be easy to feel like you’re starting from scratch. Rona cautions career-switchers and other people stepping outside of their comfort zone to remember all they did to get to that point. “Rely on your past experience and achievements,” she says. “keep in mind what you've done, what you've achieved, and how far you've come.”
Looking back on the personal and professional choices that brought her here, Rona is grateful for the risks she took and the times she proved herself. “It’s really motivating now, working in my field,” she says. “You meet some of the most extraordinarily brilliant people. They’re hardworking, and fun, and it’s hard work, but there are a lot of benefits.”
Reflecting now on her decision to join Invesco, Rona doesn’t have any regrets.
“At certain times in your life, you can afford to take more risks,” she says. “I had no reason to think I couldn’t do this—and I can.”
💎 Are you considering applying for a job at Headway? Get these tips from a recruiter to ace your interview!
📼 Watch this video to prepare for your Headway job interview. In this video, you’ll meet Brehanna Skaletski, Studio Experience Manager with Headway, who will walk you through the process and talk about some of the key questions they ask. When you are ready to apply, you’ll know exactly what the company is looking for!
📼 To ace your Headway job interview, one of the first things to know is that the recruiters are a little less traditional regarding resumes. While you will be asked to upload your resume as part of the online application process, Headway recruiters are more focused on your experience and how it can be applied to the position. Your education and exact background are not as important. What matters is showing the interviewer what you will take from your previous experiences and how you will apply it to the role that you’re hoping to get.
📼 Something to do before your Headway job interview is to become familiar with the application process. Headway has a six-step interview process that starts with an online application. From there, someone from the team will reach out for the first round of interviews. Here, you’ll sit down with recruiters who will ask questions, learn your story, figure out why Headway will be a great next fit for you, and how you and the company can build that journey together. Of course, they want to hear your questions as well at that stage. In step number three, you'll take two assessments. From there, you’ll move to skills exercise and debrief, where you can tell the interviewer what you did and why you did it. The last step is a team fit with a couple of potential colleagues. They will want you to dive in with the team who will be your new coworkers and make sure that you feel comfortable as you continue through the process. Hopefully, this will lead to step number six: receiving your hiring offer!
A Headway Job - What is it Like to Work at Headway?
Like Brehanna says: “We have this quote: If you want to go fast, go alone. If you want to go far, go together." When you join Headway’s team, you’ll get your onboarding budget to set up your home office with all the tools and equipment needed to be successful. You'll probably start with a team lunch on your first week. Don’t miss Brehanna’s insight on all the fun things the team at Headway does: from weekly lunches to traveling twice a year for company get-togethers!
🧑💼 Are you interested in joining Headway? They have open positions! To learn more, click here.
Get To Know Brehanna
Brehanna is an experienced business development manager with a demonstrated history of working in the nonprofit and healthcare industry. She’s skilled in nonprofit organizations, remote work, sales, marketing, strategy, communications, event management, organizational leadership, and management. In addition, she’s a strong sales professional who’s currently earning a Master of Business Administration (MBA) from St. Norbert College. If you are interested in a career at Headway, you can connect with her on LinkedIn!
More About Headway
Headway is looking for talented and open-minded creatives to help build software that makes a difference. At Headway, they partner with startups and corporations to craft beautiful software through thoughtful, user-driven design and passionate execution. The company values open, honest communication, transparency in all things, and collaboration while working toward common goals for the team and the clients they serve. So what’s it like to be a part of the Headway crew? They're not just developers, designers, and product strategists. They're all consultants, too. Each crew member has unique experiences and skills to help clients and Headway chart a better course for smooth sailing.