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.
In the “Great Resignation,” an estimated 47 million employees (and counting) voluntarily quit their jobs. The job market still hasn’t recovered from the unprecedented “quit rate” of 3.3% at the Great Resignation’s peak. Now, about 50% of the workforce are “quiet quitters” according to a Gallup poll — meaning, half of workers are disengaged at work and do only the minimum required of their job.
Having engaged talent is a competitive advantage for companies in today’s work environment. Replacing an employee who’s handed in their two-weeks notice can, after all, cost your company 21% of the employee’s annual salary. Employee retention strategies — ones that go beyond a box of donuts in the breakroom — are key to keeping workers engaged in the workplace. But given that overly played-out retention tactics can be ineffective at best and make your company look insincere at worst, it’s important to prioritize the right strategies. To that end, let’s go over some new and improved employee retention strategies that you may not have tried yet.
In this article, you'll find:
- Why employee retention strategies fail
- The best employee retention strategies
- Your employee retention strategy is your DEI initiative
Why employee retention strategies fail
There are plenty of employee retention strategy examples out there, but efforts can fall short. For your employee retention strategies project to be successful, you need to avoid these four common pitfalls.
1. Not delivering on promises. If you say you’re going to do something, follow up on it. Consistency is key to building employee retention strategies. Don’t ask employees to be honest about how they're feeling at work and then ignore their input. Or worse, promise big reform and fall short with token changes.
2. No trust. Studies indicate that “quiet quitting” is largely due to the relationship between employee and boss. Managers need the time, skills, and training to build solid relationships with staff. There are resource forums for people leaders to share ideas. Using tried-and-true best practices is the best strategy to build trust.
3. Siloed initiatives. Employee retention strategies can’t just live in HR. The moment they become siloed within one department or position, they fail. Employee retention strategies need to be a priority in every department and at every level.
4. No resources. Employee retention strategies need resources. To put it plainly, unfunded initiatives don’t work. Employees should be compensated for extra work such as sitting on an employee retention committee or putting together a workplace social. Likewise, pay raises and compensation should be a central part of the conversation. Remember, one of the main issues for quiet quitters is doing extra work for no extra pay.
The best employee retention strategies for 2022
With the don’ts out of the way, let’s move on to the best employee retention strategies you can start implementing today.
Listen to your employees
Well-run companies spend time and effort collecting feedback and customer satisfaction information. But what about employees? Managers need to ask, “how’s my driving?” Having data is critical to understanding how your employees are affected and making the necessary changes in order for employee retention strategies to take off. Send out an anonymous workplace survey asking about stress levels, feelings of creativity, people’s sense of inclusion, and how connected they are with their managers. If you’re not sure what to measure, start with a couple in-depth interviews. See what people want to talk about. The responses in the interviews will give you the basis for your wider survey.
If you ask your employees to be honest in giving feedback, management needs to be honest and transparent too. Acknowledge publicly the challenges the company faces based on what your employees have told you. This is the first step in accountability. Be transparent about compensation, pay raises, and benefits. Did you realize it is perfectly legal for employees to openly discuss compensation? This traditional taboo is becoming a common water cooler conversation. Social media is informing workers how to advocate for themselves. Meet them where they are. Actions speak louder than words.
Recognize and reward people, not just numbers
Over 1 in 5 employees does not feel valued at work. Feeling valued means knowing that your work is worthwhile and desirable. Watching the same sales people get rewarded for hitting their numbers again and again can be demoralizing for those who go comparatively unrecognized. Know your team and what they’re working on. Openly celebrate different kinds of triumphs, big and small, and be specific when you do. Helping people feel seen takes more than a generic “good job.”
Be flexible about work
Rethink how, where, and how long we do work. Research shows that 52% of workers prefer a hybrid remote-office work model. Employees even prefer it over a 10% pay raise. Employers must respond to this need as part of honing effective employee retention strategies.
And, as far as flexibility goes, time ownership is a massive benefit to offer employees — including by enabling them to work fewer days. Iceland is a leader in experimenting with the 4-day work week. Icelandic companies found it reduced burnout while improving work-life balance. Consider flexible arrangements that have proven results like these. Imagine how teams can be ambassadors for the company when they enjoy a new normal.
Employees that can’t see a clear career path within their company will look elsewhere to grow. The longer an employee stagnates in a position, the more their likelihood of leaving increases. Managers need to regularly work with each employee to envision their growth. Movement can be within their same position or laterally, as well. Give employees a discretionary budget for ongoing education and skills enhancement. Encourage projects and rotations with different departments to learn new skills.
Dust off that DEIB initiative
The best employee retention strategies are ones that are formed through a DEIB lens. DEIB strategies can be innovative for employee retention, as they (should) focus on all the things that make everyone supported, safe, and valued in the workplace. DEIB is, after all, not about making special accommodations for marginalized people; it’s about making the workplace better for everyone.
Your best employee retention strategy is a strategic DEIB initiativeDEIB initiatives make apt springboards for a number of successful employee retention strategies by listening to talent, creating custom work environments, and making employees across identities feel valued. Focus your efforts on DEIB, and employee retention will be one of many positive outcomes. PowerToFly has expert DEIB consultants that can help you jump start your DEIB-informed employee retention plan.
💎 Want to thrive as a customer success manager? Watch the video to the end to get some advice on how to do it.
📼Every customer success team has to follow some steps to achieve efficiency. Play this video to get three top tips that every manager in the SaaS industry should keep in mind. You'll hear from Miki Lager, Director of Customer Success at Tackle, who shares her own experience and knowledge.
📼 Customer familiarity for success. Tip #1: Know your customer. Understand their business. There are three steps in knowing how to navigate that. First, don't make it so operational. Build a true relationship with the client. Understand who are their competitors, what are the challenges they're facing, what's their true mission at heart, and how are they hoping to achieve that. Next, truly understand who the core team is that you should be working with. And finally, make sure to understand their key strategic and revenue goals.
📼Achieve customer success by delegating. Tip #2: Co-manage your customer. Not one person owns the client relationship at your company. Lead with others. Make sure to bring other stakeholders in, so that you can make sure the customer is on their path to success and that they can scale with your business solution. Team up with sales. Build a really strong relationship with your support team. Partner with the product team. The customer needs to understand where your business is headed in the future quarters so that they can plan accordingly, but also for your product team to then understand where the customer's product roadmap is headed, so you can align on strategy and best practices for that customer.
Customer Roadmap To Success - Tip #3: Define A Customer Journey
Have a defined customer journey. If the customer doesn't know where they're heading, it's going to cause some problems. Give them a clear roadmap to success. You can always adjust milestones as needed, based on different goals and different initiatives that you're working on with them. Once you have the customer journey defined, you can figure out which milestones align with the growth strategy the customer has in mind.
📨 Are you interested in joining Tackle? They have open positions! To learn more, click here.
Get to Know Miki Lager
She’s passionate about building client success teams for rapidly growing SaaS organizations. She’s been a leader at small to medium-sized companies, supporting the life cycle of startups through acquisition, and integration. If you are interested in a career at Tackle, you can connect with Miki on LinkedIn. Don’t forget to mention this video!
More About Tackle
Tackle enables software companies to accelerate and operationalize the use of Cloud Marketplaces like AWS, Microsoft, Google Cloud, and Red Hat, without the need for significant engineering resources. Their platform and team come together to make it easier for customers to build, grow, and scale their Marketplace businesses. Tackle was born and built as a remote organization and welcomes others who believe remote companies are the way companies will be built into the future. They believe that everyone has an opportunity to learn and grow in their community.
Nestlé would like to invite you to their Supply Chain virtual recruiting info session on September 29th from 4-5PM EST. Sign up for this event with leaders from our Supply Chain team to get an insider’s view on what it’s like to work at one of Gartner’s top-ranked supply chains for 2022 and the world’s largest food and beverage organization!
To say that Nazanin (Nazy) Brown and her family lead active lives is a bit of an understatement.
“We've got four young children and all of them are in multiple sports throughout the school year, as well as the summer,” she explains. “My husband and I are both coaches, so a lot of our time goes from work to home, out to the field to coach or watch games, and then back home for showers, dinner, and bed.”
With an always-on-the-go home life, it was important to Nazy to have a career that is stimulating but also allows her to be present in the lives of her children.
We sat down with Nazy to learn how she has mastered work-life balance as a Contracting Officer within the National Geospatial-Intelligence Agency while she keeps her busy household running smoothly.
From Crime TV Fan to Special Agent
At a young age, Nazy loved crime TV shows, which influenced her choice to study forensic psychology. She went on to earn a master’s degree in the subject, where she got some exposure to federal government agencies.
“During my master's degree, we had a lot of recruiters come to our program,” she recounts. “One of the recruiters from an intelligence agency told us that they often hired people from our program as special agents.”
Nazy is also fluent in Farsi, and in addition to her choice of master's program, this made her an ideal candidate for many agencies.
“I began interviewing for special agent roles based on my Farsi skills,” she reveals. “I got a few job offers, and I landed a job as an entry-level contract specialist in the private sector.”
Working for a government contractor, Nazy quickly advanced in her career and eventually became a Senior Contracting Negotiator for Lockheed Martin — and she was loving it.
“I just really liked it and thought it was a great field to be in,” she says.
And while her career advanced, so did her personal life. She became a young mother with increasing responsibilities at home, which led her to be more mindful of where she was dedicating her time.
“At that point, I was putting in so many hours — it's not a 40-hour work week,” she admits. “It wasn't uncommon for me to sometimes work weekends, especially during proposal season.”
As Nazy continued to pile on the overtime, she saw that she wasn’t able to be the mom she wanted to be.
“I wanted to be able to cut work off when I'm at home,” she recalls. “I didn't want to be that mom that comes home and is on her laptop. This was when I realized that having a job that is strictly limited to just 40 hours a week would be best for our family.”
A Parent-Compatible Workplace
Through friends, Nazy learned more about working in the public service and realized that not only would she not have to work overtime, but it would also allow her to work close to her children.
“Many agencies have onsite daycares,” she notes. “I knew that would help so much with commuting and my stress level, as well as the cost. That was my number one reason to jump into the federal government.”
So, Nazy applied for a role that looked interesting and soon found herself working as a Contract Specialist in the Defense Threat Reduction Agency. The onsite daycare took in her oldest, who was then a toddler, and promised a spot to her second child, who was on the way.
“Having my children onsite with me instead of having to drop them off in another part of the city before work every day pretty much changed my entire life,” she reflects.
With her childcare issues solved and a manageable number of working hours, Nazy was able to focus more on her career development and explore her options. It was her husband, who works in the Intelligence Community (IC), who convinced her to consider switching to intelligence.
“My husband told me that the IC is just a different animal, and he was right. The contracting is different. The mission is amazing. So I decided to look into the IC,” she says.
Applying for roles in the IC required her to rework her entire application package, but her preparation paid off when she landed a role as a Contracting Officer at the National Geospatial-Intelligence Agency (NGA).
“Since I've come to the IC, I've been able to broaden my skills,'' remarks Nazy. “It's an entirely different contract writing system, and the IC’s mission and impact are far greater in size and scope, which has really expanded my knowledge. I've learned so much in the three years that I've been here,” she says.
The Secrets to Work-Life Balance for Working Parents
Over the past two and a half years, working from home became the norm for some parents. For Nazy, this was not an option because of the sensitive nature of the data she handles at NGA — and she actually prefers it this way.
“I like the fact that I can get my work done without interruptions from my kids. And when I go home, I take my lanyard off, hang it up, and I go right into mom mode,” she says.
For other parents looking to have this same work-life balance, Nazy offers the following tips:
- Look for jobs with short commutes. Commuting to work for an hour each way might not seem like a lot in the beginning, but over time it can take a toll”, Nazy warns. “Try to get everything set up in your local area as close as you can. In an online job search, set the parameters to five or ten miles from home, max.”
- Find an organization that offers practical support to working parents. “I don't think a lot of people realize that many government agencies offer onsite childcare,” she shares. “I've had four young children who all went through them and I have nothing but good things to say about them. So consider an employer that offers this, instead of the commercial child care centers, which are double the price.”
- Have food prep on point. Between work and her children’s sports activities, Nazy can’t cook something from scratch every night of the week. “I start the week on prepped meals. By Thursday, we're finishing everything that’s in the fridge, and then on Friday we order something or go out to eat,”
- Take advantage of employer wellness offerings. “You need to take care of yourself as a mom, '' she advises. “NGA gives us three hours a week for physical fitness training, pilates, or yoga classes, which are all provided at work. Taking advantage of that during the work day is so much easier than trying to work out at home.”