From PM to Chief of Staff: How Kensho’s Meaghan Cassidy Approaches Career Growth & Continuous Learning
Meaghan Cassidy had all the cool pandemic hobbies before they were cool pandemic hobbies.
She started baking sourdough years ago. She took up yoga and bouldering even before that. And when much of America was frantically googling "how to keep a plant alive," she was caring for her thriving vegetable garden and turning its cherry tomato harvest into a delicious and easy Caprese salad (served alongside fresh sourdough, of course).
It's no surprise, then, that Meaghan has been an early mover when it comes to her career, too—or that she's continuously pursued opportunities to learn and grow on the job.
In fact, she said yes to her current role—Chief of Staff to Kensho's CEO, Bhavesh Dayalji—specifically because Bhavesh said she didn't know how to do it.
"He said to me, 'You're a great PM, but you don't know how to run a business.' I remember bristling and thinking, 'Yes I do!' But he's right. I actually didn't," says Meaghan, who has been at the AI innovation hub of parent company S&P Global for the past 18 months. "The message was, 'You don't know how to do it now, but you can learn. Would you like to learn?'"
Meaghan said yes, and we sat down with her to hear more about that decision, as well as her path to Kensho and what their learning-focused culture looks like writ large.
Stepping into—and out of—PMing
Meaghan came up as a product manager when it was still a brand new field.
"I remember being an intern and asking to have the difference between project and product management explained to me," she says.
While she got her undergraduate degree in social entrepreneurship, she spent half of her last three years of school working at a med tech startup that had her straddling marketing and product. She joined them on the product side full-time after graduating because she thought it would give her the best opportunity to learn about running a business and one day being a CEO, which is still a goal of hers.
After working at a startup in Tanzania where she was employee number two on the ground, she came back to the U.S. to take a job at a slightly larger startup back in the Boston area, where she stayed until getting to experience the volatility of startup life firsthand.
"The co-founders called an all-company meeting one Monday and told us, 'Hey, we weren't able to close our latest round of funding. Everyone's going to be laid off at the end of the week,'" remembers Meaghan.
Over the course of her career, Meaghan has learned to value companies where she can see a real path for her own growth. "It was less about what I would be doing right at the start and more about evaluating the company's mission and vision. Where are they in their own growth trajectory? What opportunities would there be?"
Kensho's work in the ML and AI space excited her, as did the company's growth plan. "I thought I'd have the room to grow and try new things without too much bureaucracy, but also have the stability of not coming into the office on a Monday to hear, 'The funding round didn't go through.' It was a really nice balance and a good mix for me," she says.
She worked as a PM for her first year, and when Bhavesh asked her to be his Chief of Staff, a new position for Kensho, she said yes without thinking twice.
In her role now, her mandate is to solve problems before they hit the CEO's desk and oversee the company's culture, including Kensho's DEI initiatives focused on creating an inclusive environment where every Kenshin feels they can bring their full selves to work. Her PM roles, which required her to translate business goals and values into product strategy and to deeply understand customer problems, have set her up well to run her suite of executive projects.
Making the most of a culture of learning
Kensho is committed to continuous learning, says Meaghan. From monthly knowledge days where engineers take a day to upskill themselves to impactathons where Kensho employees do 1-2 day projects with ESG partners, she notes there are plenty of opportunities to keep pushing yourself to learn and do more.
"There's a sense of intellectual curiosity," she says. "It's about learning, staying motivated, coming from a place of self-improvement and just being able to try things and go for it."
Meaghan credits her can-do attitude, her bias for action, and her self-confidence when approaching learning opportunities (like her new job!) to her family and other people in her life that believed in her from the get-go. Now she tries to pay that forward.
"I love telling my friends or people in my networking circles, 'Go for it, you can do this, what's the worst that will happen? You'll fail. And you'll get another job. It's okay,'" she says, also recognizing that there's privilege in being able to take those kinds of risks.
"I like to challenge myself. I like things that are hard," she says.
For those who aren't lucky enough to get a 1:1 Meaghan pep talk, we asked her what advice she has to keep pursuing growth. Here's what she said:
- Communicate your interest. "Sometimes you need help changing something to kickstart growth, and you shouldn't feel like you have to solve that on your own," she says. She recommends talking directly with your manager if you're in a healthy environment where they'd support you, or if not, finding a mentor or colleague who you can talk about career development goals with. "It can be as simple as, 'Hey, I'm looking for opportunities to be a lead on a project or learn Python.'"
- Volunteer to help. Meaghan points to a Kenshin who put a meeting on Meaghan's calendar and asked if she needed help with any PMing. "She straight up told me she was looking for more PM experience, and my response was, 'Ok, cool, what can I offload to you to help me and help you?' After checking with her manager, of course!" says Meaghan.
- "Sometimes it's just time to take a scary next step." If you feel like you've reached a learning ceiling, it might be time to leave, says Meaghan. "Eventually the time comes when you outgrow your current company. Parting ways is bittersweet, but it's also a time for celebration and reflection where you're looking back on all you've learned before you're onto something new."
If Kensho seems like a place you'd like to grow, check out their open roles!
[VIDEO ▶️ ] 3 Tips to Develop a Growth Mindset at Work
💎 Looking to boost your career growth? Tune in to catch 3 top tips to develop a growth mindset at work!
📼 Press PLAY to hear tips from Haley Wolf, Manager of the Sales Development team at Lattice. These 3 tips that she's learned throughout her own career, as well as her experience with colleagues, will help you develop a growth mindset at work.
📼 Tip #1: Request Feedback - The first of the 3 tips to develop a growth mindset at work is to request feedback from your manager and coworkers whenever you feel there is room for growth or improvement. This might be after a presentation or project, or even before that next step in your career. By requesting this feedback, you can learn what gaps need to be addressed to keep growing.
📼 Tip #2: Overcommunicate Curiosity - The second of the 3 tips to develop a growth mindset at work consists of continually asking questions. Whenever you feel you're in a pivotal moment in your career, seek advice from colleagues about their experience and even how they've overcome obstacles. Think about what you want to learn. All of this will help you grow and get career-boosting advice.
Don't Miss The Last Tip To Develop A Growth Mindset At Work
📼 Tip #3 may sound strange, but it's absolutely true: Fail Fast. What does Haley mean by that? Approach each new beginning with a fearless mindset—which will help lead to a growth mindset. When you're jumping into a new presentation or trying a new skill for the first time, think about this: probably everyone in the room has had to do this for the first time at some point! So failing fast is when we can grow the most.
📨 Are you interested in joining Lattice? They have open positions! To learn more, click here.
Get to Know Haley
Haley Wolf has been working at Lattice for 4 and a half years. When asked what her favorite part about working at Lattice is, she says: It's cliche to say, "the people," but I think it'd be wrong not to because our core values at Lattice are centered around our people! I believe that's what makes a difference here, too. And that's always stayed constant as Lattice has grown. But I think there are two elements to that. One is when the people that we're surrounded with and the people that we work with are so brilliant, so inspiring, so dedicated, with a pool of knowledge that is so diverse — that makes such a difference. But the second is the leadership team. Our exec team has done an amazing job of building that foundation that's collaborative, safe, and meaningful. I trust the decisions they make because they share everything very openly and transparently.
More About Lattice
Lattice is a people management platform that empowers leaders to build engaged, high-performing teams that inspire winning cultures. With Lattice, it's easy to launch 360 performance review cycles and engagement surveys, keep track of OKR/goals, gather real-time feedback, and encourage manager 1-on-1 meetings.
From Writer to World Traveler to Tech Lead (and Mom!)
How 2U's Liza Ramo Sessler Manages Professional & Personal Growth
Liza Ramo Sessler isn't afraid of change. In fact, she's built a life around embracing it.
From starting out her career in PR to working as a technical writer at IBM, from leaving that job to attend a coding boot camp and transition careers again, and from taking a break from being a coding instructor to travel the world for over a year, Liza is no stranger to transitioning between industries, roles, and locations.
Now, living in Austin and working remotely as a Senior Software Engineer and Tech Lead at online education company 2U Inc., Liza is navigating a different kind of change: being a new mother during a global pandemic.
But by leaning on the skills and values she's always had—like collaboration, curiosity, and a willingness to teach and learn—and adopting some new ones along the way, Liza is making these latest changes work for her, her family, and her career. We sat down to hear more about her story.
Leaning into the pivot
When she was in college at Chapel Hill, Liza was sure she wanted to work in PR. But upon graduating and moving to New York, the environment she found there wasn't quite her style.
"It was really cutthroat, and I just wasn't totally enjoying it," she says. That led to her first pivot, which was into technical writing at IBM.
"They purposefully hired people that didn't have a technical background because the content that we were writing was public-facing, and they wanted it to be as engaging as possible," she says.
While she enjoyed the role and the environment, she realized that she wanted to be building things, not just explaining them, so she attended a General Assembly (GA) boot camp on a Google scholarship.
"It's scary to not have an income for three months, but I had nothing to lose," she says. It felt like the right time to make that big switch, too. "A friend said that if you're going to make a change, do it all the way, before it's really hard to make that switch," she says. "That really helped me a lot."
Liza says she got used to "staying up all night long for three months straight—great practice for having a baby!" before being hired into her first developer role. She found the work interesting, but missed being in a learning environment, so she pivoted again and became a coding instructor for the GA bootcamp she'd graduated from.
That gave her a chance to create the kind of environment where more people could succeed.
Whether working as a technical writer or a developer or an instructor, all of Liza's jobs in the tech space have played into her natural sense of exploration and curiosity. "In PR or marketing, you kind of always feel like you have to give these really well-formed answers to things," she says. "In the engineering world, you don't have to do that. It's a really great place to scrape your knees and just say 'I don't know, let's find out together.'"
Packing up that curiosity
While working as a coding instructor, Liza decided it was the right time to make use of the travel fund she'd been contributing to for over a decade. "I had always dreamed of traveling," she says.
So Liza and her now-husband sold their furniture, packed a backpack each, and set off, traveling to 35 countries over 14 months, staying with family in Europe and Israel and visiting "as many far-fetched places as we could," says Liza.
Most impressively, Liza didn't let the stress of finding a job upon her return dim the excitement of the trip. "I just kept thinking, it's really not worth worrying about right now because I'm in Switzerland and these mountains are beautiful and I waited my whole life to do this," she says.
(It also didn't hurt that her husband is a developer too, so they opted to spend a week in a tiny coastal town in Australia and "do nothing but code and play," to get the ball rolling again.)
Finding the right environment at 2U
When Liza did come back to work, it was at Trilogy, an all-remote startup that created turnkey bootcamp solutions for universities.
When Trilogy was acquired by education company 2U, her work expanded. She's now the tech lead for student-facing products across 2U's business, which includes creating customized solutions for different short courses, boot camps, professional certificates, undergraduate and graduate degree programs.
Her work allows her to lean into the empathetic teaching she loved doing as an instructor, only now she's doing it from the inside, as an advocate for her products' users.
"At the end of the day, whether it's dealing with stakeholder requests or business restrictions or not having enough resources, it just doesn't matter—you have got to give a good product to the end users, which in our case are students," she says. "I've been an instructor and you can see the immense amount of pressure that is on those students; they have given up so much to be there and they need to focus on the content."
From building intuitive attendance tracking or assignment submitting tools, Liza makes sure her team keeps students in mind, and she takes that same energy to the rest of the company's stakeholders. "Users don't care about bells and whistles," she says, "especially because the platform here is not the product—it's really the curriculum. What our users really want is for existing features to work even better so that they can have a really easy time while they navigate through the product."
Leaning on her team
Liza is good at dealing with change, but adjusting to life as a new mom during a pandemic was a particularly big wave of change to deal with all at once.
First came the pandemic changes. Luckily for Liza and her team they were already used to working remotely from their Trilogy days. However, the extra support 2U provided was greatly appreciated.All employees received a home office stipend—which Liza used for a bike desk!—and there was regular leadership encouragement to take mental health days as needed.
Then Liza had to start planning her maternity leave. She had 12 weeks of paid leave, with an option to come back part-time for 30 days and be paid for the hours that she worked, which she took.
"I thought maternity leave was going to be like cuddling with the baby on the couch and watching a movie. And I don't think that happened once," she says. "I really needed that time to be with my little family and try to figure stuff out. And it was really nice to not have to have any work obligations whatsoever." (And, she notes, she benefitted from not even having the temptation to check in—2U's policy is to deactivate Slack and email accounts when employees are on leave.)
Most importantly, she knew she could take that time off because of how much she trusts her team. After being the only woman on the tech team at her first developer job and the only woman instructor during her time at General Assembly, she's particularly thrilled to have a more balanced team at 2U.
"The number one thing that's been helpful is that half my squad is women, so they just get it. I don't have to explain anything. It wasn't a big deal when I went out on leave. It was just like, 'No problem, I gotcha,'" she says. She adds, smiling: "And that's why it's so important to hire women in technical fields. Thank you for coming to my TED talk."
When she came back part-time, she became "very, very intentional" about how she spends her time. "If people wander off topic in meetings, I have to say, 'Yeah, we gotta get back to this or I have to leave this meeting because I have work to do, and I can't do it later,'" she says.
The development of superhuman time-management skills didn't come as a surprise, however. Her days as an instructor taught her that people with small children are the best students, and now she knows they're the best employees, too. "They have to get things done," she says.
Thanks to the environment at 2U—which affords her the flexibility and autonomy she needs to get things done on a schedule that works for her and her family—she's navigating yet another major life change with poise and confidence.
Encouraging others to embrace change
If you're considering a major life move like one of the several Liza has orchestrated over the past few years, here are her top three tips:
- Do your research. "It's not like I woke up one day and was like, 'Okay, I'm going to do this,'" she says. "It's a lot of research and talking to people; it's a calculated risk."
- Chip away at what scares you. If you're nervous to leave your current job and go into your dream field because you hate interviewing, you could do an interview—simulated or actually scheduled—every single day for 30 days, says Liza. "It sounds so gross and startup-y, but you need to find those areas where you can safely fail," she says. "Call it iterating rather than failing."
- Recognize that your career is an investment in yourself. If you'd prefer to be doing something else with your work or with your life, it's worth pursuing that. "You can start really, really small, but just start," she says.
Learn more about 2U's culture, employee benefits, and open roles.
How to Grow Your Career Without Leaving Your Company: A Conversation with Greenhouse's Lauren Allanson
Lauren Allanson has had three jobs in five years and hasn't had to move offices once.
That's because all of her recent career changes have been at Greenhouse, the hiring software company, headquartered in New York. Lauren began working there as a recruiter, then moved into product management before becoming a project manager.
We sat down with Lauren, who's now working remotely from her home state of California to discuss her career path, how Greenhouse supports her growth and what insights others can learn from her experience.
Finding her own path
Lauren first joined Greenhouse as a technical recruiter. While hiring for these roles, she interviewed hundreds of engineers, collaborated with engineering leaders and grew a deep understanding of the Greenhouse mission of helping companies become great at hiring.
After two years in recruiting, her firsthand experience with the Greenhouse product and deep understanding of recruiters and other individuals who use it made her a great candidate for a newly-opened role on the product team. Lauren had spoken to her manager about her goal to become more aligned with the technical side of the products at Greenhouse. Soon after, her manager and some of the engineering leaders she worked with recommended that Lauren consider the role. "It's so important to let your managers and other potential mentors know about your interests and skills," says Lauren. "They saw that role and thought that I would be good at it – and I might not have made that connection myself."
The learning curve in her new role wasn't always easy, but Lauren was up for the challenge. "It meant being really curious, asking lots of questions and accepting that I was not going to be an expert right off the bat," says Lauren. "It was OK that I needed to lean on other people for support while I learned the role."
Lauren soon hit her stride. As a product manager, she enjoyed partnering with a variety of internal teams and stakeholders to evolve the Greenhouse line of products. "You have to be a generalist—you're working with engineers and designers, talking with salespeople and customer success and support, as well as interfacing with your legal team to determine what impact regulations have on product build-out and interacting with customers to understand their goals and feedback," she says.
After three years in the role, Lauren realized that while she loved improving products and working with different teams, she was ready to develop skills outside of product management.
"I really enjoy organizing, planning, and executing processes, so some of the more ambiguous parts of the product role – like prioritizing feedback and turning it into a product strategy – while they were challenging and rewarding, ultimately weren't for me," says Lauren. "I was ready to dive deeper into project management and become closer to the end result."
Lauren began to take on more internal projects, serving as a project manager with the support and encouragement of some of the engineering leaders who got her into product initially. "I really loved it. I knew from that point on that I wanted to do more formal project management in the next step of my career.". Following her passion, Lauren worked to create connections internally and network with other teams to find a role that would fit what she was looking for. In the spring of 2020, Lauren found her current role as a project manager, helping Greenhouse enterprise customers implement their software and services.
"Greenhouse is very supportive of their employees' career development," says Lauren. "Both managers and employees are encouraged to discuss our goals openly and feel empowered by our culture of growth."
How to develop your career within your organization
We asked Lauren her top five tips when charting an internal growth path at your own company. Here's what she shared:
1. Network internally
"Internal connections are absolutely crucial," says Lauren. "They help you position yourself for open roles or projects, as well as help you gain the confidence to raise your hand when you see new opportunities arise." Start by volunteering for side projects in different departments and reaching out to people whose job titles interest you for a coffee chat.
She also recommends joining any groups you feel identified with where you can contribute. For example, Lauren is on the leadership team of Greenhouse's employee resource group (ERG) focused on women at work, the Greenhouse onboarding "buddy" program and the culture add interviewer team.
2. Learn how to be a good mentor and mentee
Lauren works with two organizations focused on mentorship: Minds Matter, an education nonprofit that works with low-income high school students to prepare them for college success and Built by Girls, an organization that provides female identifying and non-binary students with the support they need to make their first career move into the tech industry.
Being a mentor has taught Lauren how to be a better mentee – and helped her realize these relationships can evolve over time. "I mentored a woman three years ago when she was a senior in college and now she's a project manager who has more experience in the role than I do. She's been a huge help to me in my new role!" says Lauren. "Find those people at your organization who you can partner with as a mentor or mentee, because these relationships are also an investment in your future."
3. Invest in self-reflection
"I often check in with myself to acknowledge what I like doing within my role, what parts of the role don't resonate with me and recognize when I feel the most happy and successful," says Lauren. She recommends reflecting each month or quarter to evaluate your wins and accomplishments, areas for improvement and goals or skills you'd like to develop.
By deeply understanding her own motivations and what felt right for her, she was able to pivot towards a role that fulfilled more of her interests and strengths.
4. Create your own career ladder
"Ideally, your manager has thought about a career ladder for your position. But it's always a good idea to do your own research and think about your career path for your role as well," says Lauren. She recommends researching online to find career ladders, or developing a plan to progress into a role to ever-increasing responsibilities and salaries, for jobs you're interested in. "I identify the most important skills and then self-evaluate against them to understand where I need to gain more experience," she says. She also looks at job descriptions at other companies to gain a deeper understanding of requirements to succeed in that same role or at her own company.
5. Above all, be your own best advocate
Great managers play a big role in supporting your career development, but no one will play a bigger role in your own success and growth than you do. As you discover what you're interested in, make sure your mentors, managers and peers know what those interests are – and always advocate for yourself.
"Learn more about the team you're interested in within your company," says Lauren. "What kinds of events or programming do they do? Do they write blog posts? Do they have Slack channels? Get more ingrained in their culture in order to understand what those teams do and how you could add value," says Lauren, who has attended engineering lunch-and-learns even when they were "way over her head" in order to show that she's interested in wanting to partner with them.
When it comes to growing within your company, always follow your passion
It might seem daunting to follow a new career path within your company when so much of the groundwork is now remote, but that doesn't mean you should give up.
"All of these things can be done virtually," says Lauren. "Continue to raise your hand, show up, make yourself heard and help wherever possible to create new opportunities for yourself."
If you're interested in learning more about working at Greenhouse, view all open roles on the PowerToFly hub.
