Writer and editor who crafts stories about travel, food, feminism, and communication. Formerly at a hedge fund in NYC, currently a content-creator-at-large roaming around Latin America. Big fan of carrot cake and honesty.Find her at kathmeetsworld.com or on Instagram @kplumhoff
Tips from SeatGeek's Anuja Chavan
When Anuja Chaven turns on a fan in her house in Jersey City, she can't help but think about how every piece of it works.
"There are an extensive amount of things that have to go perfectly at the same time," says the former engineer (and current product manager at live event ticketing platform SeatGeek).
It was that interest in understanding how things actually worked that drove Anuja to study engineering—first electrical, during her undergrad in India, and then computer science, during her master's program in the U.S.
"I was always intrigued by the fact that with [software], you don't have to have a hundred people, or invest in a bunch of hardware that is costly, [but] you can still get things done and create things," she says.
We sat down with Anuja to hear more about her career, from her start as an engineer working in the banking sector to her current role as a PM at a fast-growing startup. She unpacked what it's been like to jump from the super-analytical side of things to the product management side—and gave us her best tips for PMs looking to connect with their teams (and vice versa!). Read on for her hard-earned wisdom.
From engineer to product management: the best of both worlds
Anuja's first job in tech was as a software engineer at a big bank, where she worked on solving technical problems and dealing with all of the bureaucratic red tape that came along with creating high risk tools while working in the securities lending department.
Four years and a couple of promotions in, she realized that her favorite part of any given project was the beginning, when she was scoping requirements. "I liked working to understand the business needs much more than I actually enjoyed developing technical solutions," she says.
When Anuja shared that realization with her friends in tech, they helped her see that product management might be the perfect fit for her, with its mix of analytical thinking and user focus. She took a ten-week PM course, but then faced the age-old chicken-and-egg problem when it comes to switching jobs or industries: how to get the experience needed for the jobs she wanted when all of the jobs she was seeing required that she already had experience?
A friend of Anuja's invited her to a SeatGeek event PowerToFly was hosting in New York City. Anuja went, loved the panel presentation (where SeatGeek engineers showed what they were really working on—a far cry from the closed-door siloed projects Anuja had come across in banking!), and hit it off with the recruiter. She applied for a PM role, was interviewed by a slate of people she was impressed by (including SeatGeek's CEO and CTO!), and accepted the offer when it came.
"The people I met were very, very smart, and it was such an inviting experience," she says. Now, after such a trying year, Anuja has become even more impressed by SeatGeek's culture: "They're so open about global awareness, about how you should treat employees, how employees should treat each other. They're walking the talk. It's not something that's put out and forgotten about; they're constantly working to empower and uplift those who identify with underrepresented groups." (You can learn more about this work here.)
Now, a few years into being a full-fledged product manager, Anuja is grateful for having started her career in engineering.
"Coming from that background fosters that mutual understanding of how things work. You speak the engineers' language," explains Anuja.
And that's just the beginning of the synergies.
5 things PMs should do when working with engineers
When Anuja asks her engineering team to add a new feature to a product, she knows that she's actually asking them to do a specific amount of technical work, which comes with tradeoffs and costs.
Her goal, then, is to help them understand why that work is important and let them know that she recognizes the effort required to do it well. And she does all of that in the 2-3 hours per day that she spends with her team in real-time, since most of SeatGeek's enterprise engineers (SeatGeek's business is broken down into two major units: their secondary marketplace and their enterprise business, where Anuja works, in which they build and sell a box office solution directly to clients like sports teams, venues, and theaters) are based in Israel and only overlap briefly with New York working hours.
Here are some other things Anuja does to create trust and respect between her and her team:
1. Keep engineers shielded from noise, not strategy.
Anuja spends a lot of time—up to 50-60% of her workweek, she says—in meetings. That's okay: it's her job to interface with the finance, marketing, and client experience teams that her engineering team's work serves, and meetings are part of that. Her team, however, doesn't need to have their days eaten up by endless syncs.
But that doesn't mean that Anuja keeps them firewalled away from the rest of the business. Just the reverse, in fact—she makes sure to plan several touchpoints where her engineers can get a good sense of the business strategy behind their workstreams. "You're not discussing just features, you're discussing why that feature," explains Anuja of the holistic meetings between various project stakeholders and engineers.
She also does regular stepbacks on the business's larger 3-, 6-, 9-, and 12-month roadmaps so that engineers' voices can be heard in the business planning process. "There are things that product may not be best positioned to foresee that engineering brings up, like scalability and system stability limitations," she says of their value-add. "Getting engineers involved early in the game doesn't hamper your progress but rather aids with them being in your story with you."
2. Use technical understanding to predict problems.
"There's this weird theory— a joke, really—of PMs being the dumbest person in a room full of experts, but I don't see that as being true, since you've got to ask the right questions at the right time to drive conversations between those experts," says Anuja. Not all PMs will have been former engineers, she recognizes, but a few technical skills go a long way. "Knowing the impact one team can cause on the other comes from engineer thinking abilities about problem solving, understanding issues before they actually become issues," she says. "Having that grasp on fundamentals lets you see prioritization problems quickly."
And beyond that, Anuja has had success leaning on her engineering background to build a relationship with her engineers of mutual affinity. "Having technical understanding in your back pocket creates overall trust from the engineer's perspective that you'll do what's right when push comes to shove," she says:
3. Unstick problems with other PMs before they impact engineers.
With 450 employees spread across consumer and enterprise teams, there are plenty of other PMs for Anuja to stay in touch with, and she prioritizes doing so a couple of times a week to discuss problems, talk blue-sky new ideas, and help coordinate workstreams before issues arise. "We have to be up to speed with what's going on in their world," explains Anuja. "If there's a need for something on a different team, it's helpful to be aware of it, whether you aid, assist with resolving blockers, or just stay informed."
4. Communicate visually.
"As a PM, communication is one of the best tools at your disposal," explains Anuja. "What most people may not realize is that visual communication has a much more profound impact on how strongly you can communicate to a broad, skill-set varied group of stakeholders, especially as a Product Manager."
Anuja uses systems diagrams, object diagrams, and component diagrams, among other forms of visual communication, to help get her team in sync. "Having some sort of pictorial representation of what's being discussed helps people make sure they're talking about the same thing, looking at the same vision," she says.
5. Ask engineers what their preferred choice of interruption is.
There are always going to be different types of engineers. Some may not appreciate interruptions with constant pings and Slack chats, while others might prefer real-time updates instead of having to wait for a scheduled call. "What I've been doing with my teams is just being open to asking them, 'What [interruptions] are you comfortable with? What are times that you're comfortable with?'" she says.
2 ways for engineers to collaborate better with their PMs
If the above section didn't apply because you're on the engineering side of the equation, don't worry—Anuja has advice for you, too!
1. Think of the big picture, and communicate that you understand it.
"It gives a product manager a lot of confidence if an engineer can think holistically," says Anuja. "When given a problem, try to ask about the edge case scenarios, the exceptions—that will get you into deeper discussions about how those things work."
Another great way to show that you're following is to repeat the requirement and confirm your understanding in engineering terms. "There are some tactical things you can do to improve your communication, and that's one of them," says Anuja.
2. Be open to explaining engineering concepts to your PMs.
"Don't assume your PM will never be interested in deeper details," explains Anuja, who suggests unpacking problems slowly so that both parties can be better informed the next time an issue crops up.
When it works, it really works
A few months ago, Anuja was working on one of SeatGeek's biggest projects to date: supporting the launch of schedule releases for several high-performing NFL teams. The project required that people across the entire global organization worked together to make the experience absolutely seamless so that fans could buy tickets, and so that our clients could achieve their desired revenue and fan experience goals.
"It was completely flawless—groundbreaking!" says Anuja. "Being able to see so many different streams work together and function properly was really fulfilling."
When the startup Adriana Bosinceanu was working for got acquired, things changed fast.
She went from being one of eight engineers on a small team building a streaming service to joining a company that was five times larger and had a much bigger scope.
That company was Plex, where Adriana has been working remotely as a software engineer for the last four and a half years.
As her team grew from two people to ten, Adriana decided to lean into the opportunity to grow; along the way, she found herself deepening her technical skills, her self-confidence, and her relationships. We sat down with Adriana to learn exactly how she did that, and to hear the tips she has for other engineers experiencing growth opportunities on their team.
Seeing the good
When faced with the complete disruption of the way your team works, you might feel overwhelmed, pessimistic, or even scared.
While it took about a month to get used to working on a new, bigger team and supporting a growing product, Adriana quickly saw all of the positives of her new position—including and especially all the learning it set her up to do.
"I started working with two new colleagues, and they were both such good engineers," says Adriana. "I went from an environment where I was the most senior person, and didn't really have anyone to share things with, to this place where I was suddenly surrounded by senior engineers who were very good at what they were doing."
Again, that might sound like an environment ripe for causing feelings of inadequacy. But Adriana saw it as an opportunity to learn from the best people in her field. And she knows she's not alone in having that experience at Plex.
Since the media streaming company has always been all-remote, explains Adriana, who works from a small city in Romania, that means they can pull the best-quality talent. "Whenever they hire someone, they don't have to pick the best person in the city—it's always the best person out of a much bigger pool of candidates. That means that in general, the people at Plex are pretty great, and very culturally different, and it's just a nice atmosphere," she says.
She attributes a lot of that to Plex's culture. "Every company has their values, and some are more genuine than others," she says. "In our case, one of our values is to be kind and nice to each other, which sounds very simple. But here, everyone is actually trying to be kind and helpful. [And] when you start working with people who don't act in any way like they're superior or know more or have more experience, then you don't really feel overwhelmed."
Leaning into technical challenges
Soon after Plex acquired Adriana's former employer, her team was faced with a new project: to build out the content streaming side of Plex's personal media product.
Instead of a user just being able to access their personal home videos or pictures from all their devices, this new project would introduce streaming options, from podcasts to TIDAL to live TV.
"I've been in a lot of companies where people are scared by a big change or a big feature. They try to just do the smaller version instead. And our mindset has always been to not be scared of doing the scary, big feature," says Adriana.
Her team jumped all the way in, and it paid off. "It was super fun because I was there from the start," says Adriana. "From the first line of code committed to now, years later. It really helped my confidence to be able to make decisions, to see everything grow, and to figure out that it's okay to make mistakes and to rewrite, to adapt, and to be constantly evolving."
"My technical skills have definitely grown because before I had never worked on a product that had such a scale. I never worked somewhere where we had to deal with hundreds of millions of requests a day or with huge databases," explains Adriana.
Now, being in charge of vital parts of this huge project, Adriana can look back and recognize the impact that taking on a big technical challenge with a growing team had on her self-confidence.
"I feel that now I could do anything," she says. "I could be part of any tech project, where before, I didn't have the confidence to think about myself that way. [That comes from] seeing how I could start a big, ambitious project and actually code it from beginning to end."
3 tips for making the most out of growth opportunities
If you find yourself in a situation similar to Adriana's, whether that's experiencing growth on your team, joining a new company, or facing a new, challenging project, here's what she recommends you do:
- Get to know your team and understand its dynamics. "Whenever someone joins the team, the team dynamic changes," she says. "Sometimes it's very easy, sometimes you need to adapt." Pre-pandemic, she and her Plex colleagues kept up with that dynamic by meeting up for in-person off-sites at least twice a year. "When you get together with your small team in a foreign city for a week, you have time to talk about everything and to bond, and those have really helped us a lot," she says. They took those meetups online this last year, and while some of the magic is definitely missing, says Adriana, "a week of not coding and hanging out and talking still helps."
- Be patient with yourself if you feel overwhelmed. "A lot of people feel like they're not good enough or don't have enough experience and that's just not true. That's how everyone feels," says Adriana. That's especially true if you're trying on different technical skill sets to find the ones you like best, she adds. "Personally, I switched languages a bunch of times until I finally figured out what I like. I think it's hard to figure out without trying," she says.
- If you're not getting the opportunities you want in your current situation, seek them out. "If you're unhappy, you know, [gather] some courage and apply for whatever your dream job is," says Adriana. "If you're hardworking and you like it and you're into coding, I'm sure it's going to work out."
Datadog's Lucy Williams-Jones' Unconventional Path through Enterprise Sales and Why She Wants You to Join Her Team
Like many of us, Lucy Williams-Jones' life has been deeply impacted by COVID-19.
Unlike many of us, that impact took the form of a four-day period of time where Lucy was so sick with COVID that she was sure she'd never recover—and a permanent career change when she somehow did.
Now healthy and resettled into a completely new role, the Regional Sales Director for cloud application monitoring platform Datadog chatted with PowerToFly from her home office in England's Cotswolds—"Where Cameron Diaz and Kate Winslet were in The Holiday," offers Lucy, gesturing to the idyllic countryside outside her window—to share more of her story.
The individual contributor comfort zone
When Lucy got started in sales, she was 18 and figured she'd be in the field for the length of her gap year. She then planned to go to university and pursue her goal of becoming a sports therapist for a rugby team.
"Then I found out in that first year that I could make a lot of money!" says Lucy, who ended up staying at that company, Quest, for over a decade.
During that time, Lucy was almost always an individual contributor. She liked the feeling of being in charge of her own destiny, and in pushing herself to consistently beat her goals and keep pushing for more and more success. "I was really happy smashing my number every quarter and enjoying the kind of benefits that come from that from a monetary standpoint," she explains.
Ten years in, she did transition into a leadership role and found some success there—but two things got in her way.
First, her lack of experience. "I didn't have all the tools necessary to equip my team members with," she says. "That's why I did everything rather than teach other people. I'd basically just take on their workload and change everything so that it was fit to go out."
And second, her lack of desire to keep living in Cork, Ireland.
"I wanted to come back to London and the only way to do that and earn a lot of money, which is what drives me, was to go back to an IC role," explains Lucy. She did that, and worked at a few different companies before Datadog reached out and she took an enterprise sales role with them.
"The struggle I've had with other technologies previously is that you can't demonstrate them real-time," says Lucy. "If you have an awesome platform like we have [at Datadog], when you show it to someone, you can see their eyes light up, they can see the value right away."
She was excited by the product, by the market opportunity—"it's a product everyone needs, especially as they migrate from on-prem into the cloud," she says—and by the real-life implications for clients. "When I get an Uber and the app doesn't work, I know that if they've got our software, they're going to figure out exactly where it is and it's going to mend soon, so I'm not going to get my hair wet whilst waiting for a cab—English weather, you know—while I'm waiting for the app to reboot!" she says.
Taking advantage of her second chance
When Lucy got sick with COVID in early 2021, she immediately knew it was serious. Her blood oxygen was down at 82%—the NYC health department suggests immediately going to the hospital for an oxygen level of less than 90%—but she wanted to stick it out at home. "I decided not to go to hospital because I didn't want to not come out," she says.
Lucy says that she was lying in bed, wondering what her legacy would be if she died the next day, when it hit her: she wanted a chance to pass on all she'd learned from her 22 years in enterprise sales to the next generation.
"I've learned a lot of skills that have enabled me to be successful, to have the cash to buy a forever home, go on nice holidays, explore, and travel. And when I was lying there, I realized, 'I really want to transfer these skills to young women in tech, because I think that we're an underrepresented group, and I could actually get those young women living their best lives and earning the cash that they deserve," she says.
So she reached out to her manager and told him she was ready for a leadership position. He'd been asking her to consider taking on a leadership role for a while. It wasn't until she hit her annual number at the end of the first quarter, right after recovering from COVID, and told him she was still serious about leaving behind the responsibilities she knew so well for the more complicated and less immediately gratifying world of management that he knew she was serious.
Now, three months into that transition, Lucy is sure she made the right move. "So many people have been touched by COVID this year in negative ways," she says. "For me, I feel I'm super lucky every morning when I wake up; I've taken a positive from it."
"There's been lots of learnings, but I know this is the right career choice right now. I know Datadog will support me and that I'll earn my stripes as a true enterprise leader," she says. "My focus is on passing the knowledge that I've got to other people."
To do that, Lucy has to first shore up her own knowledge. She spent her first month on the job looking closely at the business and her team and implementing changes to help everything run better, and the second month focused on measuring the impact of those changes. Additionally, she's had to get comfortable giving up control of her own accounts—"my little family," as she calls them—and managing outcomes through others.
To help her on this journey, Lucy is also brushing up on sales leadership techniques with a few favorite books, including:
- MEDDICC: The ultimate guide to staying one step ahead in the complex sale by Andy Whyte
- The Qualified Sales Leader: Proven Lessons from a Five Time CRO by John McMahon
- The Power of Habit: Why We Do What We Do in Life and Business by Charles Duhigg
- Thanks for the Feedback: The Science and Art of Receiving Feedback Well by Douglas Stone and Sheila Heen
3 ways she's building a positive culture
As an enterprise sales leader, Lucy has both the power and the responsibility to create a positive environment for her growing team. To do that, she's focusing on:
- Being thoughtful about why she's engaging. Lucy doesn't respond to emails immediately anymore. Instead, she thoughtfully considers a three-part framework before crafting her response: "I'm analyzing, reviewing, and then offering advice."
- Not saying "I need." Communication from Lucy to her team has absolutely no unnecessary urgency, she says, which is why she expressly doesn't use the word "need." "I try to make it really about, 'This is the reason why I'm asking for it, this is the benefit it's going to bring, let's work together to get something that's going to be amazing,'" she says.
- Mentoring ICs. When a SDR in Datadog's Dublin office reached out to Lucy for career advice, Lucy jumped on the chance to help her. "She's at that roundabout of, 'Do I want to go into leadership? Do I want to be an enterprise seller?' Coaching her to be the best she can be has been really, really lovely...she's successful now, but she could be exceptional."
The 3 things she's hiring for
Lucy is doubling her team size and is looking for the next generation of sales leaders to bring onboard. If that sounds like you, make sure you've got these three traits she's looking for:
- Coachability. "That's the number-one trait I look for in someone," explains Lucy. "It's the ability to take on advice and feedback and adapt. It's not saying that my way is always the right way, but it's making sure that you understand that there are different approaches. [One] of the toughest but most important parts of life is receiving feedback."
- High EQ. Lucy is looking for people who are self-aware. "You need to understand how people are perceiving you, to understand what kinds of playbooks work for you."
- Affinity for pipeline generation. "You've got to do cold outreach to new logos, but you've also got to do it in a creative manner. I've seen people doing videos and stuff, which I think is really cool; you've got to stick with the cadence and actually do it. If you don't like PG, enterprise sales at Datadog may not be the job for you," says Lucy.
Lucy has a simple motto that she has internalized throughout her career thanks to her first MD, Simon Perce: "Leave no stone unturned."
If you'd like to give 100% in pursuit of your goals alongside Lucy, check out Datadog's open roles! "I would love to build a team of strong, capable, amazing, female enterprise sales execs," says Lucy.
HR pro Rockie Lehman has two hot takes on resumes: bullet points are a must, and one-page resumes aren't.
"I'm not a big fan of squeezing everything into one page," says the Talent Manager at aerospace giant Collins Aerospace. "Don't shortcut. List all of your relevant work experience. Most applicant tracking systems nowadays automatically reformat your resume, so you can't really tell that it's two pages."
And the bullets are easy: they're a quick way for Rockie to evaluate if candidates are qualified for the job.
We sat down with Rockie to hear more tips from her 20-year career in recruiting and human resources, especially around one key principle that has greatly enriched her own career: learning to grow beyond your comfort zone.
Finding her fit
Rockie originally thought she'd be an accountant. "But after a year of nothing but numbers and statistics, it was horrible," she says, laughing. "I went to my advisor and started discussing options where I could actually talk to people and my advisor suggested management and human resources. I loved it, and I've been in that field ever since."
She first joined what is now Collins Aerospace in 2000, when it was Rockwell Collins. After 9/11, the aviation industry slowed down, and Rockie was concerned about its volatility, but she stuck it out and ended up working at various regional sites for the next 19 years.
Being embedded in different offices meant that while Rockie was focused on recruiting, she got to really expand her knowledge as a full-service HR business partner. From serving as an advisor on succession plans to working towards building a more diverse and inclusive workplace, she's taken on a wide range of projects.
Now, Rockie's main focus is on technical recruiting for the company's avionics division, bringing in new talent to join the 15,000 engineers across Collins' 300 sites. "Engineers drive our company," she says. "They're the bread and butter of our company."
Why growth matters
Candidates, whether at Collins Aerospace or other companies, have a fine line to walk, says Rockie. Hiring managers are looking for people who are excited to come in and do the job they're hired for—but also for someone who wants to grow with the organization, in whatever way is best for them.
"Leadership is an important part of our succession plan," she says. "In order to progress within our organization, you need to display leadership, in people or projects. We need people to do a job, but we need to develop people who have aspirations to grow into leadership roles."
At Collins, high-potential early-career leaders are tapped for the EnTeR program, a two-year rotational program that gets them exposure to different parts of the business.
But no matter where you're working, Rockie suggests being purposeful about how you pursue that growth and how you develop your own sense of leadership.
"In order to progress in an organization, you have to stand out. You are the only one in charge of your career. No one's going to direct that for you," she says.
Her favorite tips to do that include:
- Network outside of your immediate group. "If you're a software engineer, you might want to mentor or network with someone in systems engineering for opportunities that could lead you into a project engineering position, a technical project management position, or even management of people," she says.
- Practice executive presence. You'll look more ready for extra responsibilities if you're thoughtful about how you show up in the world, says Rockie, who suggests remembering to talk clearly and concisely, to ask questions, and to look people in the eye (or in the camera, on Zoom!).
- Join relevant professional organizations. Rockie recruits from groups like the Society of Women Engineers and the National Society of Black Engineers, and has seen how the conferences, trainings, and events that those groups put on keep people connected and top of mind for future job opportunities.
- Talk to higher ups. "They're just like you and me," she says. "They're probably more happy than your current leader to talk to you about their career, their successes, their failures. They're happy to mentor talent within the organization."
- Don't be afraid of failure. Rockie's a believer in "failing forward," a piece of advice she got from one of her own higher ups that's stuck with her. If you try something and it doesn't work, you can go back to your regular responsibilities more prepared for the next challenge.
- Know when to say no. Not all growth opportunities are created equal, says Rockie, and some projects just won't be right for you. For example, she was asked to do an extra three-month assignment and was excited to do it, but a family emergency happened at the beginning of the assignment. Rockie chose to keep the assignment, but with hindsight wishes she'd escalated out of it instead. "I really suffered from tremendous burnout and exhaustion," she says. "The biggest thing is to be mindful of how much you're willing to do, and the time that will need to be invested in the opportunity you're pursuing." If you find yourself in a similar position, try saying, "I'm not able to take this on right now, but would it be okay to revisit this in six months?"
Ultimately, Rockie has taken her own advice, explaining, "I started with Collins as a technical recruiter because of my passion for talent acquisition, but I also seek out opportunities and assignments that broaden my overall HR experience. So if and when the time comes for me to explore other options, I have the skills and knowledge in my tool belt for that next opportunity."