A Cheatsheet to Ace Your Startup Job Interview!

Ace your Startup Job Interview Tips

Startup Jobs are always in high demand – there’s the challenge, excitement and the promise of wealth creation with a growing venture. But landing the right one isn’t always easy – you need quality experience, and you have to demonstrate grit and the willingness to adapt. Explore tangible ways to ace your startup job interview, what shows off your strengths and which weaknesses can be a failure point.

“I want solid skills and a scrappy mindset,” said a Startup Founder to us while hiring his leadership team. And most others ask for the same thing, albeit worded differently.

At Maroon Oak, we work with numerous startup founders to help them hire across sectors like Fintech, Edtech, Media, Gaming, Web 3, Healthtech and more. And there’s a wealth of insight that we have gleaned from working with thousands of job aspirants in leadership and line roles. Here’s what it takes to stand out in your startup job quest. Or really, any job interview!

Plus a Cheatsheet you can save or share.

Research is a blind date with knowledge – Know your Startup!

Research Company, Competition & Interviewer(s) 

New technology or solution, or a brand new player in an existing niche, make sure you know the target company well before heading in to that job interview. Even if your role is not ‘business-centric’.

All employers, startups or otherwise, really appreciate the time you spent learning about the business. A lot of interview questions will focus on your strengths as they apply to the business context.

What to research – start with their Website, LinkedIn Posts, Press Mentions, details on Funding, announcements on recent hires. Get a sense of the profiles of  team members listed on LinkedIn. Even an investor or talent deck if you can get one.

Understand your target role’s deliverables beforehand 

Read the job description thoroughly. But don’t stop there – check out others from startups in a similar sector. The latter helps fill in key gaps especially if the role description given to you is very sketchy or too generic. 

Identity the interview questions to ask beforehand. You will have a limited window for this during the job interview, so that time is best kept for getting info that you can’t find online, like the future plans and growth path of the business and your career trajectory. 

Exploring Opportunities in your Network or on LinkedIn?

Meet Peers, and Explore Events and Resources on the

Women in Startups Community!

Thought in Action – Before you start the Interview Conversation

Review your Resume & LinkedIn

Read what you’ve written so you can be consistent on job stints (years worked, role titles), metrics achieved & data shared. Sounds simple, right?  It’s amazing how many people forget what they wrote on their LinkedIn profile. And believe me, recruiters and hiring managers are always checking these for consistency.

During her job interview, Kayla mentioned a 3 year stint with X company and the LinkedIn profile said 2 years and 1 month for the same job.

But leaving out important details is a big, or bigger miss! So many talented folks don’t bother to update their LinkedIn profiles or not adding rich detail on work, accomplishments and skills. E.g. If you’ve applied for a Product Design role, make sure you include the tools that you’ve worked with.

It’s never too late to update your LinkedIn profile, even if you’ve been shortlisted/ scheduled for the interview.

Showcase YOU with the Right Resume Skills!

Top skills to put on your Resume and 4 ways to share (with real examples)

Top skills to put on a resume and 4 ways to share (with real examples)

Rehearse crisp responses to opening + key questions

Stay succinct, concise, compact, to the point…. you get the idea.

Most rounds of interviews tend to be around 30 – 45 minutes each, and the pace of interaction is swift. We have worked with Startups where the interviewers discussed compensation and Offers in very early stages, since they liked the candidates so much. So identify your high points and practice those in brief sentences without rambling. 

Thumb Rule – the ideal response time for the ‘Tell us About You’ question should be 3-5 minutes. Other answers should be less than 3 minutes.

Example: We grew the ARR to 23 million in year 2. I had consistent success in Revenue Delivery with steady QoQ growth in customer acquisition over 18 months.

Assess & articulate your ‘selling points’ 

What is your best 1 minute response to  “why should we hire you?’ (Most startup founders don’t say those exact words, but pretty much most questions are looking for that info, so prep for interview questions in this vein).

The quality of your experience is the single most important criterion. Plus, showcase strong skills, functional tech and ease with ambiguity in a rapid growth environment. 

Do mention specifics and numbers while responding to experience questions. Can you quantify your successes, say Revenue or Pipeline or CSAT scores, team members you worked with, products you supported. Are your skills functionally deep or wide-ranging across responsibilities?

Most roles will also require a knowledge of SaaS based tools even for non-tech roles, like CRM, Design, Product etc.

Example: If the role involves P&L leadership, share your experience on delivering bottomline growth and your strategy for cost management or gross margin improvement.


Prepare for ‘why startups’ and ‘why us’ questions

Show affinity to a high chaos but strong learning environment during initial screening conversations. A lot of professionals mention that they are ‘attracted to the challenges of a startup job’. That’s great, but back this excitement with more tangible reasons. Also, with your in-depth research on the target company (as in the first point) you can add context. If you don’t know much about the business, prepare your list of questions to ask. 

Here’s an extra leg up – get familiar with commonly used startup lingo.

Concept to Validation – Articulate and Adapt your Narrative

Factor in the shorter runway to impress 

Depending on the size of the Startup, the rounds of interviews may be several or not that many. But each one will count. Even the HR screenings will be competency-focused & decisive, and since many Startup leaders and founders want to speak to only a handful of people, the elimination rate in high growth, in-demand startup jobs is extremely high.

That said, the job interview questions will vary by level and function of the interviewer. So ensure that you tailor your narrative to your audience. For online interviews, keep a cheatsheet with bullet points handy so you can circle back to your strengths, if needed.

Things to consider – size of the business in revenue and headcount, very early stage or somewhat mature, specialized role or cross-functional.

Demonstrate hands-on work approach 

A tech co-founder of a market leading Blockchain unicorn told me that he still codes and debugs regularly. Startup CMOs are known to write PR briefs and edit social media copy.

C-Suite or Managers, Startups are all about ‘getting hands dirty’ and one of the biggest strikes against candidates is hypothetical or ‘top level’ answers. Wherever possible, drill down to more granular responses on how you solved a problem or delivered an outcome. Also, even team leaders and the founding team will have a component of an Individual Contributor (IC) role in their work, and any stated reluctance to be an IC is a huge deal breaker.


Examples. More Examples. Many more Examples 

“Been there. Done ALL that. And here’s how I can do it even better!”

Ensure that most, if not all of your responses, are loaded with highly relevant instances of your work and outcomes, and challenges if there were any. Again, keep the narrative simple and honest, and speak of your contributions individually, and as part of a team.


Follow through and Course-Correct (if needed)

A candidate for a key Content Marketing role had a disastrous interview, primarily because they had not reviewed the business materials and were totally unprepared for the company-specific questions. She emailed the Hiring Manager (and interviewer) afterwards with a detailed strategy on how she would improve the business’ searchability and brand value with different content types. 

The note was solid enough to warrant a second conversation and led to a few more successful stages after that. The happy aftermath is that she loves the new company and vice versa!


Interviews can be an anxious experience for many, especially if they really need that job so a written communication works well to show your interest and competence. But in any case, a thank you note is simple courtesy so why not make it a tool to further your candidacy.

Startup Job Interviews are not rocket science, but like all important things in life, a little prep equates a great performance!

We would love to hear what worked for you, and what you had to correct or improve. Do share your thoughts.

Cheatsheet for Startup Job Interview Tips

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find top talent and build your startup team with usMaroon Oak is a Talent Partner of choice for multiple startups across sectors and geographies. If you’d like details on our hiring process and successful work, request our deck.

Pooja Krishna is a Talent Founder, Business Mentor and Mom. She has worked both in large corporates and managed startups over the last 20+ years. 

She’s  a co-founder at Maroon Oak, and is founded Win Thinks, where she writes, speaks and teaches about Skills, Brands and Businesses that scale. A day trader for over a decade, Pooja launched Trading Paces to educate amateur and pro stock traders. As a classroom mentor, Pooja loves teaching students across the U.S. about job skills and entrepreneurship. Read about her on Huffington Post and Forbes.

A trivia buff and yoga & hula hoop enthusiast, she’s discovering the pleasure of drawing Zentangle patterns for ‘creative mindfulness.’

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