I’ve got an offer on the table now and I’m trying to figure out if it’s the right move. The thing is, I can read a job description like anyone else, but those are written by recruiters and they all sound the same. I need to know how to separate the offers that will actually build my skills from the ones that’ll feel like I’m treading water.
The community has been helpful here—people keep mentioning things like org structure, reporting lines, and the types of projects flowing through the team. But I want to get more specific. What signals actually matter when you’re comparing two different corporate strategy opportunities?
One is at a larger, more established company where strategy reports into the CFO. The other is at a growth-stage company where strategy sits closer to the CEO and product team. I know the day-to-day will be different, but I’m trying to understand which path actually sets me up better for what comes next. Is one clearly better for learning, or does it depend on what I want to do after this?
For anyone who’s evaluated multiple offers like this, what criteria did you actually weight when making the call?
The reporting line is critical, but it’s only half the story. At a growth-stage company reporting to the CEO, you’ll see how strategic decisions cascade through the organization and you’ll likely have broader scope—but the role may also be less defined, which means more unstructured work. At an established company under the CFO, your work is more measurable and financial rigor is non-negotiable, which is valuable training for corporate discipline. Ask each organization: what was the most successful strategic initiative in the last two years, and who drove it? That answer tells you whether strategy actually influences decisions or just supports them. For your next role, consider what skill gap concerns you most—if it’s financial analysis and business case rigor, go CFO. If it’s speed and adaptability, go CEO-line.
Consider these specific metrics: First, budget allocation—what percentage of capital are they actually deploying based on strategic recommendations? Second, strategic initiative pipeline depth—how many substantive projects are underway versus planned? Third, stakeholder composition in strategy meetings—are functional leaders present, or is it isolated? Fourth, promotion precedent—have previous strategists moved into CEO-adjacent or board-level roles, or out of the company? These data points suggest whether the role compounds your skills or plateaus them.
real talk—ask them about their biggest strategic miss. growth-stage will tell you they pivoted too slowly on market dynamics or missed a competitive threat. established company will tell you about execution failures or organizational silos. whoever has a clear, non-defensive answer to that question actually learns from strategy work. the other one? they’re probably just going thru the motions either way.
this is so useful! so like, asking about their biggest failure tells you a lot? that’s kinda clever lol, hadn’t thought to approach questions from that angle.
Both paths will teach you so much! Trust your gut on which culture feels right—growth-stage for speed, established for systems. You’ll crush it either way!
also check if anyone’s actually left the role for something better. if all previous strategists are still there doing the same thing five years later, that tells you it’s either a dead end or people get too comfortable. neither option’s great for someone trying to build momentum.
Career velocity is measurable through promotion timelines. Request the promotion history for strategist roles—average time to manager or principal level, typical tenure in role before exit, and exit destinations (internal promotions, external C-suite, industry transitions). This data reveals whether the role is a launchpad or a holding pattern.
ok so you’re saying like, find out if people actually get promoted from strategy or if they just stay there? that’s def a sign i should investigate more before saying yes.