CKO Day 1 full script Flashcards
1) Introduction: The AI Marketing “Space Race” has begun
“Good afternoon, Team! First of all - I’m super excited to be here chatting with you all for another amazing Company Kick Off. [engage the audience]
We’ve heard from the majority of the Exec team today and what’s clear to me, and hopefully to all of you, is that we are on the cusp of a meteoric shift in the world of Marketing driven by AI. To be clear, leading this shift is not something we want to do, it is something we MUST do or we will be left behind.
To paint this picture more clearly and given today’s space theme – I thought I’d compare this shift to another pivotal era of innovation. The 1950s Space Race was all about who could be the first country to land someone on the moon. While we often recall NASA’s ultimate victory in landing the first person on the moon, it wasn’t always their race to win. Many people forget, but it was the Soviet Union (modern day Russia) that sent the first person into Space… and once that happened, it became clear: we were falling behind and we were losing the race. And our response wasn’t slow, or gradual… It was urgent, focused, and bold. At the time our rockets were still exploding during takeoff, but JFK made a bold proclamation that we would not only get to space, but we would land on the moon by the end of the decade before anyone else.
The first step was forming NASA (or as we at Attentive would say “Space MBRs”), which brought together the best minds, the right resources, and the necessary funding under one mission. With a clear goal, they moved fast, rapidly testing and refining new technology. This relentless drive led to the Apollo program and, ultimately, the first moon landing.
Fast forward to today’s Space Race – the AI revolution in marketing is transforming how brands connect with their customers. Hundreds of software companies are inundating marketers with how they have incorporated AI into their solutions. Our moon landing is no longer about making an incremental improvement in efficiency– it’s about reimagining personalization, automation, and engagement at scale. The companies that fall behind in this Race will be forgotten, while the winners will become world class public software companies. Our mission is to harness the power of AI to deliver unprecedented 1:1 personalization for all of our customers”
2) Revolutionary companies set ambitious Goals
Building a revolutionary company starts with ambitious goals.
In 2025 our goal is to launch our rocket and break through the atmosphere. In this case, breaking the atmosphere means targeting a milestone of $750M in ARR, with over $100M coming from our new products, over a 2.5X increase from 2024. This will give us the momentum to achieve our ultimate goal.
Because we… like NASA… don’t want to just break out of the atmosphere, we are trying to land on the moon. …and for us, that means achieving $1 billion ARR by the end of 2026, with $250M from new products like AI, over a 6X increase from 2024.”
Building a revolutionary company and accelerating growth is not easy. But the people in this room are not here because they chose the easy path or are willing to settle for mediocrity. As John F Kennedy said about the space race: “We choose to go to the moon in this decade and do the other things, not because they are easy, but because they are hard.”
3) Phase 1: Building Our Rocket Components
To get to the moon we first needed to assemble our rocket. This was a lot more difficult than it looks. This was Phase 1 of our AI multi product journey to the moon.
NASA had to make a lot of tough choices for their mission. Urgency and focus were key. They couldn’t choose to do everything. But 3 critical modules were chosen: navigation, propulsion and life support
- Navigation: had to move spacecraft through space at 18 miles/second to a precise location on the moon which was also moving
- Propulsion: A rocket heavy enough to carry a lunar module had never achieved the velocity to break through earth’s gravitational pull
- Life support: They needed a capsule for both to and from the moon and while they were on the moon
Each of these had to be developed and tested independently but ultimately all needed to work together for the rocket to function and enable them to land on the moon.
Over the last few years, we’ve been building the key components of our rocket—including SMS, Email, AI —and that process hasn’t been easy. Each product has required deep research, continuous customer feedback, and countless iterations to refine and validate each component.
While some competitors chose to try and build every product, we knew we had to make hard choices to build the things that really mattered.
Just like engineers test each part of a rocket before full assembly, we ensured each component was strong enough on its own before integrating them into the unified system that Keri walked us through earlier.
4) Navigating the Flat Part of the S-Curve in 2023 and 2024
“Last year at CKO, you heard me talk about S-curves. As a reminder, the S-curve represents a typical pattern of growth over time… beginning with slow initial growth, followed by rapid acceleration… that eventually levels off as a product matures in the ecosystem and reaches some point of saturation.
The early flat part of the S-curve is where the real challenge lies and is the hardest part of Phase 1. It’s the phase where progress feels slow, and the work often feels tedious–sometimes even thankless. You need to develop and refine new products, work on positioning and support and make a lot of mistakes along the way.
Attentive had gotten so used to being the market leader in SMS with the best product, it was a big but necessary adjustment for us. We saw this firsthand with some early iterations of our Email product… when we convinced 15 Wunderkind customers to migrate to Attentive Triggered Email in 2023… and 13 of them churned within the year due to performance.
And while that was very painful and made some people hesitant to sell and buy our email product at the time, it forced us to take a hard look at what was missing…
5) Building momentum: Flywheel
So how did we get through the flat part of the S-curve and break through that initial gravitational pull?
In thinking about navigating the flat part of the S-curve, I often come back to the analogy of the flywheel. A flywheel is a self-reinforcing system that feeds into itself and gains momentum over time.
Two core characteristics of a flywheel are: 1. It’s incredibly difficult to get them moving at first and 2. Their power comes from multiple inputs working together– no single factor drives their momentum. Getting each of our rocket’s components to function has often required re-building the flywheel each time for each product.
This process requires contributions from every single team in the room:
Starting with building a prototype or alpha, securing early adopters, gathering feedback, and refining the product based on insights. This phase can be challenging, especially if customers don’t immediately see the value– something we’ve experienced many times over… These early setbacks can be discouraging, and it often takes several iterations to get right…
As our product proves its value, we determine pricing and packaging – what is it worth? Marketing then sharpens messaging about our product, creating Sales Plays, QBR decks, and other materials to drive engagement, and expanding awareness and adoption with prospects and customers.
At this stage, we start to cultivate some organic traction– a happy customer at an event might share their success with Attentive with a prospect and help us win a new logo. Developing partnerships with Agencies and Tech Partners becomes easier, leading to new integrations and joint solutions that help us become stickier.
All to say – every single person in this room plays a vital role in building the flywheel– whether you sit in Sales, Legal, BI, EPD, Marketing, CS, RevOps, Finance– each of you contributes to building the momentum necessary to launch.
Its all about how you respond to adversity to get through this phase. Lets go back to that Wundkerkind example from 2023. Did we give up? No! We ultimately refined and smoothed our offering to overcome the initial resistance we were facing. The result? Last year, we were able to steal one of Wunderkind’s biggest customers, Decker’s, in a 3-year, $1.8M dollar triggered email deal. Moving past this initial friction is hard, but once we learn and improve, we are set up for massive future success. We have now won a number of large 6 figure triggered email rip and replace against Wunderkind worth millions of dollars
After two years of hard work, why am I so excited? Because we are moving past the flat part of the S-curve…and the good news is that the farther along it we go, the faster our flywheel turns and the more momentum we build. As we rocket up the steep slope of the S-curve and break through the atmosphere, we should feel our headwinds transform into tailwinds as we lose that gravitational pull.”
6) 2024: Phase 1 success
“We are not just seeing success in Triggered Email. We’re starting to feel those tailwinds today in a variety of areas. We are winning breakthrough deals in a variety of areas. A few milestones I wanted to share:
Email sign-ups surged, with over 800 customers launched on our solution in 2024– a near 100% increase from 2023. To call out two logos on the slide:
Carter’s is our largest Email deal ever at $3.6M TCV over three years. This SFMC rip and replace took over 12 months to close, with every team playing a role in this win. We’re developing App Push this year, in part to support this deal.
LG – last summer, we unexpectedly lost our champion—a strong Attentive advocate in a sea of Marketing Cloud supporters. Despite being mid-contract on SMS, they launched an RFP in Q4 for their ESP business, putting our renewal at risk. We swarmed the deal, bringing in teams across the org—agency, engineering, procurement, marketing—to build confidence in Attentive from every angle. Not only did we win over a new set of decision-makers, but we also sold them on our AI vision, securing AI Pro mid-cycle. The result? A massive $600K+ TCV win.
Our AI-driven solutions saw ARR growth skyrocket from $0 in 2023 to $21M in 2024, cementing our position as the leader in AI-powered messaging and setting the stage for even greater growth ahead.
H&M – we closed our biggest AI deal yet with H&M —an $830K AI Pro TCV with a $1 CPC on AI Journeys (could be $60K p/ month) as part of a three-year renewal. This win was driven by a deeply aligned decision-making team that fully bought into our company’s vision, reinforcing the strength of our AI strategy and long-term value.
We cemented our leadership in the RCS rollout at NRF in New York, with the event we hosted with Google– continuing to demonstrate that we are the market leader in mobile shopping. We already have 5 approved customer brands, with over 40 others on a waitlist.
Crocs – This is one of our biggest renewals this year, and we’re actively working to secure it. Crocs is one of only five customers approved to beta RCS ahead of its launch, a key advantage we’re leveraging in renewal discussions. Our partnership with Google is a major milestone—one we should be flexing across the board.
I personally think RCS leadership could be one of the most impactful things we do this year to cement our positioning as a leader in mobile messaging.
These significant wins are not just isolated successes…”
7) Winning Phase 2 is the real prize
Less than 1% of startups get to $500M revenue, and only a fraction of those are able to evolve to a successful multi-product business to continue to scale to a $1B+.
While the last couple years didn’t always feel like winning, it’s important to zoom out… because when we compare our trajectory against Hubspot, one of the most successful public multi-product B2B companies of all time it becomes undeniable as we almost doubled their Phase 1 trajectory. We are not just winning big deals— the chart above is proof that while the early stages our tough, our strategy is working and that accelerated growth is ahead of us..
8) Phase 2: Unifying our Components to break through the atmosphere
“Our mission this year is to break $750M in ARR, and we’re going to do that by bringing all of our rocket components together. This is Phase 2 of multi-product growth. That means unifying our narrative and truly operating as a multi-product company– which Keri walked us through earlier.
A major challenge for us last year in Phase 1 was figuring out how to bring all the components together– and we were kind of doing it on the fly…. Testing and learning what worked. We were pitching SMS, and then Email… and then AI… and then AI with Email… and all of a sudden RCS became a thing.
Phase 2 is where things all come together. Phase 2 should feel easier but it is not something we should take for granted. New challenges arise: company positioning, client discovery needs to evolve, bundling and other pricing changes, etc. These require new processes, teams and approaches. E.g. we launched the Account Director team this year to help us unify selling all new products and renewals under one team for our large Strategic customers.
The greatest impact here is that the whole becomes greater than the sum of its parts. E.g. our number one reason for churn is consolidation for email; our second is a perceived lack of differentiation of our core SMS product. Selling email and AI helps solve both of these. So we not only drive expansion revenue from the new products, we will keep more customers from leaving Attentive. This is creates a compounding effect for getting our Net Dollar Retention to 120%+. That is the real engine of our growth.
We saw this in action with Taylor’s conversation with Carter’s.
9) Customer-Centric Approach (Part 1)
We now live in a world in which our customers can start from multiple jumping-off points and we need to meet them where they are. To win, we need to take a customer-centric approach and become masters of discovery across products and features– deeply understanding our customers’ pain points and strategically positioning the right components of our platform at the right time…
This requires us to shift our mindset from selling individual products, or components, to thinking holistically about our customers… acting as consultative partners who can help them navigate their needs in this rapidly evolving era.”
10) Customer-Centric Approach (Part 2)
“…And when we do this well– when we keep the customer at the center–their journey becomes clear and the path forward feels much more simple. By aligning our products to their unique challenges and goals, we can guide them toward the solutions that will drive the most impact. This clarity not only fosters stronger, more trusted relationships with our customers, but it also empowers us to deliver results that truly matter to them. Ultimately, this approach is what sets us up for success in 2025 and beyond, ensuring that we not only meet but exceed their expectations at every step.”
11) Finish the Mission
“NASA’s success in the Space Race was built on their ability to innovate, take risks, and collaborate in ways that had never been done before–both within the organization, as well as within the community, universities, private companies, and the public sector. They didn’t just launch rockets… they redefined what was possible by combining groundbreaking technology with relentless problem–solving, prioritzation and urgency.
I am very proud to say that success at Attentive has been defined by a similar set of qualities – creativity, bold ambition, and a relentless commitment to pushing boundaries. And we’ve succeeded not just because of our technology, but because we’ve embraced the power of partnership–working together internally… as well as with customers, partners, and agencies–to aggressively pursue new opportunities and meet our customers where they are.
It is this mindset that makes me confident about the milestones we need to hit… and just as NASA did, we will continue to tackle tough challenges head-on, with the same spirit of innovation and collaboration that got us to this point.
As I said at the beginning, we have no choice but to accept this challenge and to win this challenge. As JFK said about winning the space race: “that challenge is one that we are willing to accept, one we are unwilling to postpone, and one which we intend to win”
If we can do that, we can break through the atmosphere and have a real shot at landing on the moon.
Let’s Finish the mission.”
