8 Red Flags When Interviewing for Demand Gen Roles
(That Could Save Your Career)
Three months into what seemed like my dream demand gen role, I was spending more time in alignment meetings than actually driving pipeline.
The job description had checked every box. Series B, B2B SaaS company, solid funding, "own the demand generation strategy," hella competitive salary. I thought I'd hit the jackpot. I found myself really romanticizing the opportunity, the growth potential for my career, the outcomes I’d get to drive. All of it.
Instead, I found myself in back-to-back meetings (no seriously…for this company I had 27 hours of RECURRING meetings each week. Not to mention the ad hoc calls as well) trying to convince sales that marketing wasn't just a lead factory, explaining to the CEO why our MQL numbers didn't translate directly to revenue, and defending budget allocations for experiments that leadership didn't understand. Sound familiar?
The problem wasn't that I was bad at my job. The problem was that I'd completely failed to do my due diligence on what this company actually needed from demand gen—and whether that aligned with the type of work that energized me.
👋 Hi, it’s Kaylee Edmondson and welcome to Looped In, my newsletter exploring demand gen and growth frameworks in B2B SaaS. If you’re one of the 19 people that have subscribed since last Sunday, hello! So glad you’re here—you’ve just joined 2k+ marketers who read Looped In every Sunday.
Here's what I wish someone had told me before I took that role: there's one critical step that most demand gen professionals skip entirely when evaluating opportunities. Before you can identify red flags, you need to understand your own DNA. And by that I really just mean your natural preferences.
Know Your Demand Gen DNA First
Demand gen isn't just demand gen. The work looks completely different depending on where a company sits in their growth arc. What energizes one person absolutely drains another.
I learned this the hard way when I moved from a scrappy Series A startup where I was building everything from scratch, to a more established company where I was expected to optimize existing systems. Same title, completely different work, and I was miserable for months before I figured out why.
The Many Eras of Demand Gen
The Scrappy Era ($0-$20M ARR)
This is where you're MacGyvering programs with duct tape, gut impulse, and maybe a thousand bucks a month for variable spend. Your "tech stack" might be a combination of HubSpot's free tier, a bunch of Google Sheets, and whatever creative workarounds you can dream up.
You're typically not just the demand gen person—you're probably also doing product marketing, content creation, event planning, and some sales enablement. Your budget conversations involve fighting for an extra $80/month for a new tool.
The work looks like: Cold outreach sequences you write yourself, manually tracking attribution in spreadsheets, hosting "webinars" that are actually just Zoom calls with 12 people, and celebrating when you generate 5 qualified leads in a week.
You'll love this if: You get energized by creative problem-solving, you don't need a ton of structure to be productive, and you want to see the direct impact of every single thing you do. You're the person who thrives on turning constraints into competitive advantages and early wins.
The Scale-Building Era ($20M - $50M ARR)
Now we're talking pretty real budgets and actual systems. You've got product-market fit figured out (at least in a segment or two), a clearer ICP, and leadership that understands the difference between marketing and sales.
This is the experimentation playground. You can finally test that account-based campaign you've been wanting to run, implement an attribution method, and build repeatable processes that don't require you personally touching every lead. But your teams have also grown a little larger at this stage — meaning there will be more layers of approval and feedback needed to get things shipped.
The work looks like: A/B testing email sequences, building multi-touch attribution models, running paid campaigns with optimization budgets, and implementing marketing automation that goes beyond basic drip campaigns.
You'll love this if: You're energized by turning chaos into systems, you love rapid testing cycles, and you get satisfaction from seeing clear ROI on your experiments. You're the person who geeks out over funnel optimization and conversion rate improvements. And you don’t mind a few extra alignment meetings to make sure everyone is on the same page.
The Specialization Era ($50M+ ARR)
Welcome to sophisticated demand gen operations. You've got real budgets, specialized team members, and agreed-upon attribution models. Your martech stack probably costs more than most people's salaries.
The wins are measured in percentage improvements that translate to massive absolute numbers. A 2% improvement in conversion rates might equal hundreds of thousands in additional revenue.
The work looks like: Coordinating multi-channel campaigns across multiple touchpoints, managing complex scoring models, running ABM programs with dedicated support, and optimizing insights across long B2B sales cycles.
You'll love this if: You prefer depth over breadth, you enjoy mastering sophisticated tools and processes, and you get energized by technical complexity. You're the person who loves building solutions to complicated problems, and ensure cross-functional alignment with various stakeholders.
Here's the crucial part: there's no wrong answer here. I've seen brilliant demand gen professionals burn out because they took roles in the wrong era for their working style. The series A founder who gets frustrated by process-heavy environments. The systems builder who withers without clear structure. The optimization expert who feels lost without sophisticated tools.
Whichever era got you excited just reading about it-that's your demand gen DNA.
Let’s talk red flags
Now that you know what energizes you, let's talk about the warning signs that should make you run…or at least ask very pointed questions.
These are all drawn from either personal experiences or challenges I’ve stepped in to solve on behalf of clients. By no means is this list exhaustive so apply your own lens here and figure out what your red flags are (ideally before you start the interview process to avoid biases).
Universal Red Flags (Run, Don't Walk)
#1: Marketing-Sales Dysfunction
What it sounds like: "Marketing passes leads to sales, then sales complains about lead quality, so we're hiring someone to fix the process."
Why it kills you: You'll spend your time mediating between teams instead of generating demand. I've seen demand gen professionals spend 60% of their time in "alignment meetings" trying to get marketing and sales to play nice.
The question to ask: "Walk me through your last [X] closed-won deals and tell me how marketing and sales collaborated on each one."
If they can't give you specific examples of collaboration, or if the story involves a lot of "handoffs" instead of ongoing partnership, probably a red flag.
#2: Inability to Articulate Company Story
What it sounds like: Vague mission statements, generic value propositions that could apply to any company, or "we're like [successful company] but better."
Why it kills you: You can't create compelling campaigns without a clear narrative. I once worked with a company that took 45 minutes to explain what they actually did, and then couldn't tell me why someone would choose them over competitors.
The question to ask: "Tell me about your last [X] wins and specifically why those customers chose you over alternatives."
If they struggle to answer this, you'll struggle to create effective messaging.
Stage-Specific Red Flags
Early Stage Red Flags
#3: Unrealistic Scale Expectations on Zero Budget
What it sounds like: "We need to 10x our pipeline but marketing budget is staying flat" or "We want to move upmarket with our existing messaging and offer."
I had a Series A founder tell me they wanted a demand gen program that would "generate 500 MQLs per month" with a $2,000 monthly budget. That math doesn't math, and taking that role would have set me up for failure.
The question to ask: "What's your current customer acquisition cost and how do you expect that to change as we scale?"
#4: Over-Complicated Tech Stack Dreams
What it sounds like: Detailed wish lists for expensive martech tools they can't afford, or expectations that you'll immediately implement an attribution model that solves all their problems.
Why it matters: Early stage is about scrappy execution, not perfect measurement. If they're obsessing over tools instead of talking about creative outreach strategies, they don't understand the stage they're in.
Scale-Building Stage Red Flags
#5: No Clear ICP Definition
What it sounds like: "We sell to mid-market companies" or "anyone who needs [generic solution]" or my personal favorite, "we have a few different ICPs we're testing."
At Series B/C, you should have figured this out. If they can't describe their ideal customer profile in detail, you'll waste months (and budget) figuring it out for them. But really this often means they have deep rooted alignment issues (most often at the exec/leadership level) about what they’re actually trying to be, and for who.
The question to ask: "Describe your best customer today—not just company size, but specific characteristics that make them a great fit."
#6: Still Obsessing Over Strange Measurements
What it sounds like: Success metrics focused entirely on lead volume, not pipeline quality or revenue influence. Or we care about lead/MQL volume, the rest will follow.
If they're still talking about "generating more MQLs" instead of "improving pipeline velocity" or "increasing conversion rates," or “marketing’s impact on pipeline”, they're stuck in outdated thinking. You’d likely spend most of your time on internal education trying to bring them along for the ride vs getting to execute, ship, and learn. (At the same time if internal education and alignment is your thing, go for it.)
Specialization Stage Red Flags
#7: Outdated Data Practices
What it sounds like: Manual reporting processes, no clear attribution model, or data living in silos across different tools.
At this stage, sophisticated data operations should be table stakes. If they're still doing weekly manual reports or can't tell you their attribution model, you'll spend all your time fighting infrastructure instead of driving revenue impact.
The question to ask: "Walk me through how you currently measure marketing's influence on pipeline and what your stack looks like for attribution."
#8: Demand Gen Viewed as "Top of Funnel Only"
What it sounds like: "Marketing owns lead gen, sales owns everything after that" or "we don't expect marketing to influence expansion or retention."
Modern demand gen should touch the entire customer lifecycle. If they view you as just a lead generation engine, you're missing out on the most interesting (and highest-impact) parts of the role.
The Interview Strategy
Here's a few other ways to uncover these flags without being obnoxious about it.
Questions by Company Stage
For Early Stage Roles:
"What's the biggest constraint you expect demand gen to work within?"
"How do you currently measure success when attribution tools are limited?"
"What's worked better than expected in your current go-to-market approach?"
For Scale-Building Roles:
"What experiments have you run that completely failed, and what did you learn?"
"How do marketing and sales currently share accountability for pipeline?"
"What's your biggest bottleneck in converting leads to customers?"
For Specialization Roles:
"What's the most sophisticated campaign you're currently running?"
"How does demand gen collaborate with customer success on expansion?"
"What would success look like for this role in 12 months?"
Red Flag Discovery Questions
Ask these regardless of stage:
For Marketing-Sales Alignment: "Can you give me a specific example of how marketing and sales worked together on a deal last month?"
For Company Story: "If I asked your best customer why they chose you over [specific competitor], what would they say?"
For Realistic Expectations: "What's the biggest challenge the person in this role will face in their first 90 days?"
For Growth Philosophy: "Tell me about a marketing initiative that didn't work and what you did next."
Some Stories from the Trenches
The Scrappy Mismatch
A friend of mine left a Series C company to join an early-stage startup because she wanted "more ownership." What she didn't realize was that the startup expected her to also handle customer support, write blog posts, and manage their social media accounts.
She'd gotten used to having specialized team members and sophisticated tools. Going back to wearing 47 different hats felt like a step backward, not forward. She lasted four months.
The Scale Trap
Another colleague moved from a bootstrapped startup where he'd built everything from scratch, to a Series B with "real resources." Turned out their idea of resources was a bunch of expensive tools that no one knew how to use properly, and processes so rigid that launching a simple email campaign required three weeks of approvals.
He went from shipping daily to shipping monthly. The bureaucracy killed his momentum.
The Specialization Success
But here's a good one: I know someone who made the jump from a mid-stage scale-up to a public company's demand gen team. She was nervous about losing the "startup energy," but it turned out she loved the sophisticated attribution modeling, the complexity of architecting multi-touch campaigns, and the resources to test everything properly.
She's been there three years and keeps getting promoted because she found her sweet spot.
The 48-Hour Rule
Because if you’re like me you might like to romanticize new marketing opportunities, after every interview, give yourself 48 hours to process what you learned. I like to write down:
What excited me most about this conversation?
What made me nervous or skeptical?
Do the challenges align with my strengths?
Would I be energized or drained by this work in 6 months?
Most people make the mistake of focusing only on title, compensation, and company brand. But the day-to-day work is what determines whether you'll thrive or burn out.
Your career is too valuable to waste time in the wrong company.
I learned this lesson the hard way in that alignment meeting nightmare role. The company wasn't inherently bad—they just needed someone who got energized by aligning internal politics. That wasn't me at that stage of my career.
The best demand gen roles aren't the ones with the fanciest company names or biggest budgets. They're the ones where your working style aligns with what the company actually needs, where you can make real impact instead of managing politics, and where the daily work energizes rather than drains you.
Perfect roles don't exist, but strategic role selection makes all the difference.
Which era of demand gen work gets you most excited? I'd love to hear about your experiences—the good, the bad, and the alignment meeting nightmares (please tell me I’m not alone 😅).
See ya next week,
Kaylee ✌