For many product marketers, a C-Suite position is akin to a soccer player winning the World Cup, an actor scooping an Oscar, or a musician picking up a Grammy.
Earning a seat at the top table of product marketing requires hard work, graft, and determination. Oftentimes, it can be difficult to grasp an understanding of what a C-Suite role actually entails - until now.
We’ll be chatting with C-Suite members who’ve successfully stepped up to the plate at their respective companies.
To kick start the series, we're speaking with Derek Osgood, Founder & CEO of Ignition.
A little bit about Derek
Derek Osgood is an experienced brand marketer with an entrepreneurial mindset and has extensive experience in leading teams at startup companies.
A versatile practitioner, Derek combines analytical, strategic, and creative approaches uniquely that sets him apart from many tech marketers. Whilst working as a Marketing Executive and Consultant, Derek delivered double-digit monthly growth consistently, across a variety of markets and business models.
Derek’s experience isn’t limited to the world of startups - he’s also worked with video game giant Playstation. He’s a specialist in a range of areas, including Go-to-Market, segmentation, product positioning, user acquisition and engagement, integrated offline marketing, digital performance marketing, creative development, and product management.
In our chat, Derek discussed:
- His roles and responsibilities as a member of the C-Suite at Ignition
- Whether he feels product marketing is a suitable route to C-Suite jobs
- His route to the C-Suite
- Whether the reality of C-Suite jobs matched his expectations
- What to prioritize in the first 90 days as a C-Suite member
- Aligning goals as a C-Suite member
- His C-Suite icons
- Managing expectations as a C-Suite member
- C-Suite challenges
- Best practices when engaging with the C-Suite
- How to improve relations between product marketing and C-Suite representatives
- Securing C-Suite support as a product marketer
- Collaboration between product marketing and C-Suite members
- Advice for pursuing C-Suite jobs
Roles and responsibilities
Can you please provide an overview of your role and your responsibilities?
I'm the CEO and founder of Ignition - a platform helping PMMs manage Go-to-Market processes end-to-end - I do everything at this stage! 😂
Although this mirrors the product marketing role quite a bit right now as we work through early positioning, messaging, and our Go-to-Market strategy.
Preparation for C-Suite jobs
Because product marketing is such a multi-faceted role, do you feel it sets people up well for C-Suite jobs?
Absolutely. In my opinion, product marketing is the best role to set you up for success in the C-Suite, as it gives you unparalleled visibility into what every team within the organization is doing, their needs, and their operating model.
It also fosters a degree of customer-centricity and strategic thought which is often lacking even in polished executives from other departments.
Derek’s route to the C-Suite
What did your path to the C-Suite look like?
I started my career in entertainment, launching big AAA games as a Product Manager at PlayStation. That role looked a lot like product marketing, or traditional brand management from CPG where it was marketing-oriented but had full end-to-end P&L responsibility.
However, I’ve been in and or around venture-backed startups ever since. I was head of marketing or product marketing for a bunch of early-stage startups in every vertical you can imagine, from messaging to payments to field service management.
Then, I did some corporate innovation stuff running marketing across a portfolio of companies in BBVA’s fin-tech innovation arm launching and scaling companies we’d either incubated or acquired.
Recently, I was one of the first couple dozen folks at Rippling where I stood up the product marketing function as we went from 0 to about $20M in annual recurring revenue (ARR).
I’ve straddled a lot of stuff from product marketing to growth to product management. Interestingly though, a big part of why I got into product marketing in the first place was my desire to be a CEO.
I felt like product marketing was the best possible function to learn how to become a great strategist because more than any other role it just sits at the center of everything. You see how all the moving parts within a company come together, from product strategy to UX and design, to growth, to sales.
Product marketing was a gateway drug for me to start my own company, and to give back to the role that shaped who I am today.
I happen to have decided to make my company one designed to help product marketers navigate probably the most agonizing part of the job - launching products.
Expectations vs reality
How has your experience working in a C-Suite role compared with your initial expectations? Is there anything you wish you knew beforehand that would’ve helped you perform?
I’ve been an exec for many years, so I kind of had a reasonable idea of how things would shape out and haven’t had many surprises in this current role - although being a founder carries its own set of craziness!
I think the biggest shock though when moving into a C-Suite role for many people is how important transitioning from “giving direction” to “inspiring via leadership” becomes.
You need to get good fast at focusing less on the specifics of things that need to get done, and more on painting a clear picture of vision, objectives, expectations, and operating models, then trusting your team to chart the best path forward within those guard rails.
Priorities in C-Suite jobs
What would you say are/should be your priorities for the first 90 days as a C-Suite member?
First, you need to get a lay of the land – you need to deeply understand your team, and other teams’ current priorities, operating models, and challenges. That way you can formulate a clear picture of the state of the business and where bottlenecks lie.
From there, you really need to identify whether problems are people problems, process problems, or product problems and put together a plan to address them. Also, be sure to publish these thoughts to the C-Suite – convey your assessment of the state of the union and an actionable plan for how to address it, in the interests of seeking out feedback on that plan.
From there, often your next biggest priorities are going to be appropriately resourcing your team via hiring, new tools, or putting folks into roles more aligned with the new objectives you’ve identified.
Aligning goals as a C-Suite member
How do you align departmental goals and objectives throughout the company to facilitate short and long-term success?
Ultimately, you should have an OKR process (and please make sure you’re not mistaking KPIs or deliverables for strategic objectives), in which company-level goals are set for the quarter/year, and then you’re cascading strategic objectives for the team to help impact those quarterly.
How you’re balancing near and long-term objectives come down to judgment around prioritization – if things are existential threats in the near-term, you should be prioritizing around them, but in 70-80% of cases you should be optimizing for things that are going to drive maximum impact over the mid and long-term.
Derek’s C-Suite icons
Which C-Suiters did you look up to before you got your role?
I spent much of my early career following and working closely with a CMO named Terrence Sweeney. He’s “done it” in a huge range of businesses and stages, and just really knows his stuff.
He’s been a huge inspiration. Also, as much as I disagree with some of their ethics, at a purely operational level I admire Jeff Bezos and Mark Zuckerberg’s ability to set a clear, top-level vision and rapidly identify/operationalize movement on new opportunities.
Managing expectations as a C-Suite member
How do expectations of you change when you’ve made the transition into a C-suite role?
The whole bar raises. You’re on the hook, for everything, and there’s no more room for excuses.
If a team member or initiative is underperforming, it’s not their fault, it’s yours. The expectation is that you know things that are/aren’t working, and are already actioning them before anyone else even becomes aware of them.
You’re also expected to model good behavior for everyone in the company – it’s no longer acceptable to do potentially detrimental things like participating in office gossip.
What were some of the biggest challenges you faced en route to your C-Suite role? How did you overcome them?
Imposter syndrome! If you’re progressing the right way, and you’re self-aware of how you’re doing, chances are you’re going to be in a near-constant state of realizing you have significant skill or knowledge gaps and you’ll constantly be uncovering things you “didn’t know you didn’t know”.
That makes it challenging to manage yourself, (which is the most important job of any exec, before managing others.
I made a conscious effort to seek out mentors who I could have candid conversations about this stuff with, and also have always pursued lifelong learning to try to fill those skill gaps.
C-Suite best practices
What do you consider to be the best practices when engaging with the C-Suite?
Be direct. Tie everything back to objectives. Clearly define the challenges driving your recommendations, and specific, tangible actions you can take to overcome those challenges. Talk in numbers and make sure you know the numbers off the top of your head.
Improving relations between product marketing and C-Suite members
What can product marketers do to ensure C-Suite members fully appreciate their value?
Tie everything back to real business impact. Use data where possible and/or “case studies” from real-life examples for the things that are squishier.
For example, if the positioning is an issue, survey customers and asks them to articulate your positioning back to you and try to quantify what % of them align with the positioning you’re hoping to create.
Alternatively, if sales enablement is a focus but you don’t have a lot of data, tell a story of a salesperson you provided an asset to and how it helped them close a deal.
Securing C-Suite support as a product marketer
What advice would you give to product marketers in an organization if a C-Suite representative isn’t fighting their corner higher up the ladder?
First, have a conversation with that person. Tell them about how it's impacting your ability to do your job, and thus the downstream business impact of that.
If that fails, see if you can find another C-Suite member who can/will advocate for you, and maybe even consider asking to reorganize product marketing under them.
For example, if your CMO doesn’t understand/advocate for you; maybe the CPO is deeply feeling the pains product marketing solves and will be more likely to advocate for you.
Alternatively, if sales are drowning and need more support, the CRO will be your champion.
Collaboration between product marketing and C-Suite members
How often do C-Suite members directly interact with the product marketing team at your company?
I’m the CEO and Product Marketing Manager, so every day!
At past companies, though it’s been less frequent than I would have liked, typically the CMO and I would talk daily, but conversations with other C-Suiters were often more like weekly or monthly.
It’s on you as a product marketer to drive these interactions though – set up weekly or bi-weekly meetings with critical C-Suite stakeholders.
Advice for securing C-Suite jobs
What’s your golden piece of advice for product marketers hoping to reach a C-Suite position?
Stop being reactive and speak up – see yourself as a leader/owner and take every opportunity to drive strategy instead of simply enabling strategy.
Also, don’t forget to tie it all back to tangible numerical business impact (revenue, retention, etc.).
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