“Women can’t be in tech” — really?
From Ada Lovelace to Grace Hopper to Adele Goldberg, women have proven that they not only belong in the tech and MarTech space but can also create their own legacy.
In my conversation with Christina Brady, CEO and co-founder of Luster, she says, “In an industry where fewer than 5% of startups founded by men have female CEOs, the rarity speaks volumes.” Well, Christina didn't wait for an invitation to the table – she built her own as the co-founder and CEO of Luster.AI.
Christina’s journey into the tech industry is one of resilience and adaptation. She transitioned from sales roles to becoming a leading figure in AI-driven sales enablement. With 15 years of experience in tech, she brings a unique perspective on the challenges and innovations driving the tech and MarTech space.
This interview is part of G2’s Professional Spotlight series. For more content like this, subscribe to G2 Tea, a newsletter with SaaS-y news and entertainment.
What’s your favorite beverage?
If we're talking about alcoholic beverages, I'm all about the classic Manhattan. When it comes to non-alcoholic options, I love my sugar-free energy drinks — I practically run on them!
What was your first job?
My first job was when I was 14 years old. I worked as a secretary at the art school where I took my art classes. When the classes became too costly for my mom to afford, I started working in the front office to help cover the costs of my painting classes.
What's your favorite software or software category in your current tech stack?
One software that has truly made my life easier is Canva. Being an artist, you would assume that I would be good at designing. However, I'm not naturally gifted at designing presentations or thinking creatively in that format. Canva simplifies the process by allowing me to create stunning presentations quickly and effortlessly, which saves me from the blank canvas syndrome.
What problems at work make you want to throw your laptop out the window?
The biggest challenge is when I'm caught in a cycle of back-to-back meetings. By the end of seven consecutive meetings, I often feel like I'm even further behind. After being on calls the entire day, I find myself drowning in 400 emails and 300 unread Slack messages. And then I need to pick up my child from school. It's ironic how the more I try to keep up, the more overwhelming it becomes, and that sometimes makes me want to toss my computer out the window!
Can you tell us a bit about yourself and how you got started in the tech industry?
Sure! I've been in sales for about 17 years. I lost both my parents in my early 20s and became homeless. I realized that my initial career choice wouldn't provide the financial security I needed. I was then able to get hired and work as an insurance salesperson, and I learned that I loved selling but did not love what I was selling. While I discovered my passion for sales, the product didn't resonate with me.
Later, the tech boom of 2009-2010, during which I was living in Chicago, changed the game for me. With companies like LinkedIn, Salesforce, and the then-emerging Groupon making waves, I seized the opportunity to pivot. I applied for an account executive role at Groupon, facing a daunting 60-person group interview process. It was wild! But they saw something in me and hired me, marking my entry into the tech world. It has now been 15 years since that!
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Wow, 15 years in tech! That’s an incredible milestone. As one of only 15% of female tech startup founders, what challenges have you faced, and how have you overcome them?
The biggest challenge is that when there aren’t many people you can ask for advice, and when there aren’t a lot of folks who have lived what you've lived, it's difficult to get advice specific to what I need. As a woman in the predominantly male domain of AI venture-backed technology, finding a supportive network that truly understands my journey is difficult. My background is somewhat unconventional for this industry. I am neither an engineer nor a product developer. Instead, I embody the user demographic I'm creating solutions for, which sets me apart.
There are all kinds of difficulties, from trying to get time in the room to secure funding to trying to compete in an industry where you don’t have a lot of women. Sometimes, it can feel hard just to get a leg up and be heard and taken seriously. As a minority within this group, I encounter many of the typical barriers associated with being underrepresented.
Despite having an unconventional background, you have made a strong presence in this space and proved to be a thriving leader. How have your roles at your previous companies shaped your approach to leadership and innovation at Luster.AI?
My approach to leadership is clear and open communication. It is deeply rooted in my extensive background in improv theatre. For over 12 years, I performed with Improv Olympic and Second City and participated in various conservatory and theatre programs. These experiences honed my ability to think quickly, pivot effortlessly, listen attentively, and assess situations accurately. This experience has shaped how I interact and collaborate with others.
My leadership style has evolved drastically since my first role at Groupon, where I was promoted to manager from an account executive and had to manage a team of 30-35 people who were once my peers. I believed being a leader meant having all the answers and never admitting uncertainty. This mindset led to isolation, burnout, and the feeling that leadership might not be for me.
My mentor, Bill Bartlett from the Sandler group, helped me explore various facets of professional communication and effective leadership. That proved to be a turning point for me. I became fascinated with workplace dynamics, delving into concepts like radical candor and DISC assessments. I’ve actively used this approach while building Luster.AI. It helped me create a more transparent and candid relationship with my team.
For example, I have regular open sessions where people share ideas and give feedback, and we also indulge in various activities that help us learn each other’s strengths and weaknesses. This deep dive transformed my take on leadership, making me a more attentive listener and a better leader.
And now, as a leader at Luster.AI, I am passionate about fostering a values-based culture. I strive to create an environment where individuals feel authentic, respected, and empowered. We prioritize open communication and address issues constructively to build a supportive workplace.
Drawing from your extensive leadership journey, you've likely encountered a variety of challenges and growth opportunities within the industry. What common skill gaps have you noticed in sales teams, and how does Luster.AI effectively address these gaps?
A common challenge is when we fail to identify the unique individual skill gaps until those gaps have already affected key areas such as our sales process, revenue targets, or customer retention. This is where we must decide which skill gap is most detrimental so we can retrain staff and aim for better outcomes in the future.
As someone who has progressed from an account executive to a frontline leader, I have found it difficult to pinpoint what's preventing us from achieving our revenue and performance goals. This often results in guesswork: is the problem with our sales process, methodology, objection handling, or demos? We never truly know, and this uncertainty drove me to create Luster.AI.
At Luster.AI, we assess skills at an individual level — be it for a sales rep, customer success team, or business development representative. It creates a skill proficiency map that highlights each person's strengths and areas for improvement, enabling us to predict where potential gaps might impact. As someone who experienced this lack of visibility firsthand, I realized that even when gaps are identified, addressing them could take months without adequate resources.
So Luster.AI is meant to not only uncover skill gaps that are stopping you from hitting revenue but also help you proactively address them.
What do you envision for the future of sales enablement, and how is Luster.AI preparing to lead in this space?
What I have observed recently is many talented professionals in enablement, learning and development, leadership, and coaching find themselves trapped in reactive situations that affect their effectiveness. The goal is to shift from this reactive fire drill approach to a more strategic one.
“The future of sales enablement is all about being prescriptive, proactive, and predictive”
Christina Brady
CEO and co-founder of Luster.AI
Imagine if enablement teams could measure each individual in their organization, identifying gaps and inefficiencies. This would allow them to create a proactive and predictive roadmap for training and development. Based on data-driven insights, they could recognize what sort of programming to implement throughout the year. Decisions like who to bring in as a guest speaker or what Monday's team training should focus on would be informed by this data.
From a sales leader's perspective, having a prescriptive, individualized coaching plan for each team member means knowing exactly where potential issues might arise. This level of insight allows leaders to meet their team members where they are, providing personalized coaching and training to address skill gaps. The ability to maintain a real-time pulse on team dynamics is already yielding positive revenue outcomes.
Looking to the future, the potential for teams to grow, scale, and develop with this newfound capability is thrilling. We are on the cusp of unlocking an entirely new era of sales enablement and leadership, where data-driven strategies lead the way. This promises to revolutionize how we approach sales coaching and team development, opening doors to possibilities we have only begun exploring
What was a recent challenge you faced with your existing clients in helping them increase their revenue? How’d you help them overcome it?
One significant challenge currently affecting many companies is tool fatigue.
Many organizations have spent hundreds and thousands of dollars on different technologies meant to support their teams administratively or in revenue creation.
However, this has led to burnout issues, as sales reps, CSMs, BDRs, and managers are often required to juggle 10 to 20 different tools every single day. These tools frequently lack integration, resulting in low adoption rates and frustration from a management perspective.
On top of that, every three to four years, we see a shift in how buyers buy technology. A lot of times, companies don't follow that shift. They stick to very rigid sales processes and methodologies that no longer serve their customers, but the change feels too much of a task. And so where we're trying to intersect is make sure that we have a tool that is very specific, very simplistic, and does something easily measurable.
Moreover, we aim to equip teams with actionable insights that cut through the noise, enabling them to focus precisely on what's necessary to drive immediate results without the burden of excessive administrative tasks or sifting through complex data.
“Today, simplicity is key — the more user-friendly the tool, the better.”
Christina Brady
CEO and co-founder of Luster.AI
As we enter 2025, what do you think are the biggest trends in AI that will take over the sales landscape?
There are two big trends in AI right now: its potential to replace human roles and its capacity to support and enhance them.
A couple of companies have come out with technology where AI takes over tasks traditionally performed by humans, such as AI-driven sales development representatives (SDR) designed to conduct sales outreach, or AI systems that generate marketing emails and create promotional materials.
I think there's a lot of nervousness and hesitation around those kinds of tools and around this trend. First, people inherently don't want to be replaced by a machine. And they don't have to. And secondly, there's the fear of what if I replace my entire team with an AI robot, and then it doesn't work.
However, in the second trend, you have tools that are not meant to replace a salesperson. They are meant to give them a metaphorical treadmill to help them be the strongest version of themselves. And so there you have AI helping with administrative tasks, helping people to acknowledge gaps, helping to coach them, and helping to train them.
So, these two main use cases in AI are the big ones that we are seeing, and at times, they sort of compete with each other a little bit.
What are your thoughts on maintaining a proper work-life balance and having your own time?
For me, it’s actually different. I am one of those people who embrace a lack of balance. I don't think that things are going to be balanced. Instead of balance, I focus on making meaningful decisions and sacrifices that align with my personal and professional values, leaving me content and justified at the end of the day.
Being deliberate with your time is essential. At the end of each day, I aim to make the best decisions that minimize regret and propel me toward my goals.
“Setting clear objectives for what success looks like in various roles is vital. Determine how you want to allocate your time to these goals.”
Christina Brady
CEO and co-founder of Luster.AI
If you aim for just balance, you might spend the rest of your life feeling like a failure. It's trying to measure a fish's ability to climb a tree. Einstein said that, and he was right. You have to be able to accept the fact that balance isn't going to happen, and the minute you let go of that restraint that you're putting on yourself, it just becomes about being deliberate and being happy and successful in a lack of balance.
Last but not least, what advice would you like to give to young entrepreneurs, especially female entrepreneurs who aspire to lead in the tech and MarTech space?
One of the most important principles of effective leadership is understanding that you don't need to have all the answers or excel at everything. Your primary role as a leader is identifying what needs to be accomplished and determining the best person for each task.
It's not about handling everything yourself or knowing every solution. It's crucial to embrace the ability to say, "I don't know," and focus on surrounding yourself with individuals who complement your skills and fill any gaps.
So be aware of what you're good at and your zone of genius, and then be completely open and modest about what you're not good at. Find brilliant people to surround yourself with. Let them do their job and stay focused in your zone of genius.
Follow Christina Brady on LinkedIn to learn more about her journey and how she is transforming the world of sales enablement.
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Edited by Supanna Das
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