If you’re trying to grow your brand while ensuring every marketing dollar drives ROI, you’ll want to read this.
When you’re the first marketer at a growing company, you don’t always have the luxury of long-term planning.
You’re scrappy, reactive, and just trying to make things work.
That’s how things started at Jobber when Nick Keyko was the Head of Marketing and started to build everything from scratch.
I sat down with Nick to get a behind-the-scenes look at how Jobber gets customers, plus how they grew to $100M+ ARR sustainably and predictably by building a content brand.
I can’t wait for you to apply these insights to your own company.
What you’ll read here are words. Some Nick’s. Some mine.
— Brendan
Below, we’ll explore:
- How Jobber transitioned from reactive to structured marketing planning.
- The key hires and strategies that fueled their rapid growth.
- Unique philosophies that shaped Jobber’s marketing success.
1. How far out do you plan your marketing in detail, and how has that evolved over the years?
When Jobber’s marketing team started, it was just Nick and an intern, operating on a month-to-month basis.
In those early days, it was just sort of running on all cylinders, just trying to get stuff out the door a month at a time.
Over time, the team grew to about 6 marketing generalists and started to stabilize. We were able to look at our day-to-day and say, “okay, what are we doing this month? And next?”
At the time, the company had a 10-year vision, which was big and audacious, but it was great because we could see where we were going.
Our CRO, who had a marketing background rather than sales—a rarity in the field–mapped out a pretty detailed 3-year strategy. This plan integrated sales, marketing, customer success, and business operations.
With that 3-year plan in place, we were able to develop quarterly tentpoles, where we knew what was happening every quarter and how to slot things in.
One thing I found that worked really well was allocating specific percentages of time to different activities. For example, when planning an event, I could set a clear expectation with our brand and community team—starting with dedicating 20% of our time to it, which might then scale up to 80% as the event approaches.
From there we developed a solid quarterly cadence where we were working together to plan out what the next quarter and beyond was going to look like.
And then, you know, as the team gets bigger, everybody just gets a bit better at it, right?
2. For marketing strategy, who comes to these meetings, who runs the meeting, and how often do you meet?
We had a core belief: “The best idea can come from anywhere.”
For instance, one of our most successful programs, Jobber Grants, came from a suggestion in a monthly team meeting by an individual contributor. The program has since grown to giving out 20 grants totaling $150k annually to small businesses.
Once an idea like this comes to fruition, we dive deeper into the process.
First, we discuss how the plan might work and determine the necessary budget. This stage is a great opportunity to collaborate with the team by outlining planning steps, resource allocation, budgeting requirements, cost of acquisition, and how we measure success.
This planning phase is also a valuable teaching moment. Once the company strategy is set each year, I review the marketing strategy to identify the key priorities. From there, we develop strategies to address these priorities, followed by specific tactics.
I involve my direct reports in the high-level brainstorming process. They then take these ideas back to their teams to discuss tactics. For example, if the goal is to increase awareness, the strategy might involve events, social ambassadors, or other programs. The teams refine these tactics and then report back for final strategy alignment.
One of the most important aspects is ensuring that every team member understands how their work contributes to the overall goals. But at the same time, it’s crucial for a startup to have a top-down strategy.
You can’t just let everyone run wild and do their own thing because, ultimately, marketing has to tie back to where the product is going and how it supports sales targets. You can’t achieve that with purely bottom-up planning—it has to be balanced with a clear top-down strategy.
Everything we did had to drive ROI. A major unlock for us was a strong attribution model, allowing us to measure how different programs contributed.
Attribution is never perfect (every model is wrong, just in different ways), but agreeing on our framework let us make better tradeoffs, and as a leadership team, we need to clearly communicate tradeoffs.
If we’re doing A, B, and D, but not C, we need to explain why.
3. How many marketers do you have? How has that team changed over time?
By the time I left, we had 60+ marketers.
In the early days, most hires were local (Edmonton), but as we expanded, we added a Toronto office and remote team members.
Company culture was a huge focus. Our CEO and CTO obsessed over it, spending significant time reinforcing company history and mission. Perks like office beer and ping-pong were nice, but the real culture came from a deep connection to small business customers. We brought customers in for panels, shared their stories, and ensured our team felt the impact of their work.
Who Were the Best Early Hires?
- Data & Analytics Expert – There was no biz ops team in the early days, so we needed someone who could track spend and payback periods.
- Creative Lead – Early investment in design helped Jobber stand out visually.
- Deep Generalist – Someone who could flex across roles was invaluable.
- Community Builder – No community existed for home services. A simple networking event turned into a powerful differentiator.
Who Were the Best Later Hires?
- Creative Director (ex-Red Bull & Shopify) – Managing creatives is different than managing marketers. This role helped streamline execution and bring creative ideas into the business strategy.
- Project Managers – As the team scaled, process and traffic control became crucial.
- Video & Design Team – A field trip to Home Depot helped designers better understand our blue-collar audience and tailor branding accordingly.
4. Do you structure your team around channels, products, user types, user journey, outcomes, or something in between? Has this changed over the years?
Team structure evolved with company strategy but had core areas:
- Demand Gen – Paid and highly measurable digital efforts.
- Product Marketing – Bridged marketing and product.
- Lifecycle Marketing – Initially part of product marketing, later needed its own leader.
- Community/Brand – Social, events, ambassadors, PR (eventually “Brand & Comms”).
- Content/SEO/Web – Managed web presence and organic growth.
- Growth Team (for a time) – Combined engineers + marketers before spinning out to product.
- Centralized BizOps – Provided marketing support.
We did no outbound—100% inbound-driven growth
5. What is the difference between average marketing leaders and those who are able to attract, hire and retain top talent?
Every time I leave a meeting with marketing leads at Pendo.io I’m reminded that for all the focus on new tech, data, KPIs, emerging strategies, the CMO job ultimately comes down to hiring. Get hiring wrong, and none of that stuff matters. Get it right, and all of that stuff begins to fall into place. – Joe Cernov
Great marketing leaders spend 50% of their time on strategy and 50% on hiring & retention.
You also have to genuinely care about your team’s development to ensure they’re growing as fast as the company.
If the company is expanding by 100% year over year, then individual skill sets should be developing at the same pace. As a leader or manager, it’s your responsibility to ensure that happens. This means providing constructive feedback, offering one-on-one coaching, and identifying and removing blockers.
Growth-stage startups are different at every level. The scrappy generalists who thrive on a 10-person team often struggle in a structured 60-person org.
Leaders need to recognize that and have open conversations about career progression—even if that means helping someone find their next gig elsewhere.
6. What’s your primary tool for tracking tasks and campaigns? And for production?
From what I recall, every team had its own system. We used Google Sheets for planning while other teams used Asana.
I think you can overcomplicate project management systems unless there is a dedicated project manager.
What I need from my team is simple: we’ve already agreed on what we’re doing—now I just need to know if things are on track or off track.
If something is off track, we need to have a conversation about it. If it’s on track, I don’t need to spend much time on it because there’s always enough that isn’t going according to plan and requires attention.
I held weekly one-on-ones with all my direct reports, and those meetings were theirs to lead. They were expected to bring the most important topic to discuss first—whether it was professional development, a personal challenge, or a project that was going off the rails.
Beyond that, we had a weekly marketing leadership meeting focused on what was working, what wasn’t, and what needed to be communicated to the broader team, and then our quarterly planning sessions.
Honestly, that structure worked well—it kept us focused on solving the right problems while ensuring we were always moving forward.
But I think it’s [project management tools] almost overkill for a lot of marketing teams because the most important thing is getting people to talk. Instead of relying on a tool, real conversations—whether face-to-face or over a call—are always more effective. It’s better than just asking, ‘Hey, did you check the assignment?’
7. Is there something unique or philosophically core to how the marketing team and leaders think about acquiring customers?
Community.
Everything we did had to add value to small business owners’ lives—not just sell software.
Most of our audience was still using pen and paper, and no one else was truly advocating for them. We built content, events, and programs that genuinely helped, and it paid off.
Also, we never aimed for “good” work. It had to be EPIC—something that cut through the noise.
8. What were the best performing channels for you? Did that change over time?
Early on, paid search & SEO were the backbone, targeting industry + feature keywords (e.g., “landscaping invoice software”). But over time, we realized we needed to create demand, not just capture it.
Brand programs became critical—events, grants, partnerships, and micro-influencers (industry-specific, 10K followers, high engagement). Those efforts built long-term awareness and made Jobber a household name in the industry.
9. What other questions do executives ask each other that often aren’t shared publicly?
That’s a good question.
Executives spend a lot of time talking about company culture—especially in a fast-growing startup when you’re adding a lot of new people to the mix.
The challenge is that you don’t always know how well things are actually going. So a big part of the conversation is, how do we keep up with that?
I think what most executive teams worry about is that they’re wasting a bunch of time on things that aren’t important, right?
That’s where a lot of the back-and-forth happens—marketing pushing on product, product pushing on sales, and sales pushing back on marketing. Someone says, “Our close rate is 20%,” and another asks, “Why isn’t it 50%?” These conversations can get really tactical, really fast.
But the best executive teams are always looking 12, 18, 24 months ahead. Because at some point, you’re no longer steering a small ship. The company is getting bigger, and even a tiny change in direction today can have massive consequences down the road.
I like to use a space analogy—if you’re just a centimeter off at launch, by the time you reach Mars, you’ve completely missed the planet by like a freaking light year
So yeah, a lot of the discussion is about exactly what you’d expect—hiring, budget, long-term planning. But underneath all of that is the bigger question: Are we actually headed in the right direction?
How to use this info:
1. Send a DM to your teammate: “Lindsay — I read about how Nick Keyko ran the Marketing team during his time at Jobber. I thought there were X things in there that might really help our team. Mind if I send them over?” Then send her this link.
2. Meeting with your boss: “I just got a behind-the-scenes look at how Jobber grew their marketing team from 2 to 60+ while surpassing $100M+ ARR sustainably and predictably, this might be worth bookmarking.
3. Linkedin Post: How to avoid missing your target by “a freaking light year” – An in depth look at how Jobber grew their marketing team from 2 to 60+ while surpassing $100M+ ARR sustainably and predictably. (make sure you connect with Nick!)
Thanks for reading!
This is the 15th of a long series.
If you have a tip or feedback, I’d love to hear it.
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