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16 ways to stand out in a hiring process

Real tactics candidates have used successfully, one new Chief of Staff req we're working on, 3 new job opportunities, a candidate close-up, and more


But First, 3 Shower Thoughts:

  1. Strategic storytelling has extremely high utility and as such should be a more common skill.

  2. Delirium Tremens is an amazing beer but the brand name literally means “severe alcohol withdrawal”.

  3. What did we even laugh at before memes?


How to Stand out as a candidate

Let’s jump right to it! Below is a list of tactics that candidates have used successfully in their hiring process to stand out (including myself when I was applying for Chief of Staff roles back in the day):

Shooting your shot

If you’re at this stage, you’re wondering how you can get the attention of the founder, internal recruiter, or someone else at the company who’s on the hiring team. Here are things you can do in order of most sane —> insane.

  • Cold email or DM them. Keep it short and sweet. Use bullets where you can. Don’t just talk about what you’ve accomplished in generalities. Quantify them, and tie them to bullets on the job description. Make it very, very easy for whoever you’re DMing to see that you’re a fit.

  • Venmo them 2 cents. It’s fairly easy to find someone’s Venmo username. Everyone has their Venmo alerts turned on, and everyone will look at a notification about someone sending them 2 cents. At the risk of coming across creepy, it guarantees to get eyeballs on you, and it’s your opportunity to “share your 2 cents” as to why you’re a good fit for the role. I’m pretty sure this is within PayPal’s “Acceptable Use Policy”, but double check before doing something that can get you kicked off the platform. (But…nothing ventured, nothing gained, and sometimes it’s better to ask for forgiveness than ask for permission.)

  • Make them an offer they can’t refuse.

Before your interview

  • Buy or trial the product. Nothing says “I actually care about your product/business/problems” more than handling the physical product or going through a user journey as a new customer, where applicable. It gives you a ton of ammo going into your interviews, whether with respect to answering your interviewer’s questions, or asking your own. Which leads me to my next bullet…

  • Do your research on the company and interviewers alike. It’s very likely that the founder’s thoughts are memorialized online via some medium — whether that’s a video interview, their own writing on Substack or LinkedIn, a written article, etc. Referencing something you previously read or heard with your interviewer will pleasantly surprise them.

  1. What you're great at

  2. How you've leveraged that to deliver X, Y Z results

  3. What you're working on improving

  4. What drives you nuts

  5. What your quirks are/what makes you weird

  6. Your personality type (Enneagram, Myers-Briggs, Working Genius, etc.)

  7. What you value in a leader Most people won't do this, but it's such a good conversation starter, and frankly, a great hook in a cold outreach as well.

  • Create a 30/60/90 day plan. If you’re headed into a later stage interview, jump the gun. What better way to show your proactivity, ownership, autonomy, and excitement for the role than drafting up one of these bad boys? It shouldn’t take you long — if you asked solid questions, you have some good insights from your interviewers, and can essentially evolve the JD into a 30/60/90. It doesn’t have to be a masterpiece. They won’t be expecting it, so you can make a solid impression if you go in with this.

  • Become a good storyteller. If you’re not clear on your why, you won’t be able to communicate it, much less get your interviewer to understand it. Make sure your career arc, transitions between roles, and impact you’ve driven are clearly articulated and aligned with your overarching career objectives.

During your interview

  • Always think “how does what I’m about to say demonstrate extreme ownership, a roll-up your sleeve mentality, and the ability to build 0→1?”. Whether it’s about difficult conversations you’ve had or how you got thrown into the deep end on a project and not just survived, but thrived, how do your accomplishments tie to these core character traits and skills? These are far and away the top things early-stage startup founders look for in Chief of Staff candidates. EQ, polish, and maturity rank very high as well for Level 4+ Chief of Staff roles.

  • Link your accomplishments to the job requirements. As SpongeBob once said, bring it around town:

Now that you’ve seen it, it cannot be unseen.

Obviously, JDs code the challenges that the company is facing in the role responsibilities and it’s highly likely that their biggest ones are in the first couple of bullets. For example: implementing new processes and systems is code for “information is silo’d and we can’t find what we need quickly, and because of this, X, Y, Z is suffering”.

If an interviewer asks you a very broad question like “tell me about your work experience”, you must connect the dots for them. You have to tell the relevant story, not just any story. Your most recent experience is likely the most relevant, so spend more time there. When discussing your accomplishments, bring up how they align with the requirements for the role. Bring it around town.

  • Ask insightful questions. Spend time preparing. Non-obvious questions stand out to interviewers because they rarely hear them. While important, “What are the benefits?” isn’t as interesting as “How does the founder set the example for the culture they’re building at XYZ company?”

After your interview

  • Send a personalized thank you note to your interviewer. Do it within an hour of your interview. Use it as an opportunity to reiterate your interest or expand on something specific your interviewer said about the product, company, culture, growth, role, etc. This brings me to my next tactic…

  • Don’t waste the opportunity to add value at each touchpoint. You have the interviewer’s attention for at least as long as they’re reading your email. What can you share with them that they would find valuable? Something else about you, like a writing sample (or maybe your user manual? :)) Something interesting you read recently? It’s another opportunity to jump the gun and make things easier for them to say “yes” to you. If it’s later in the process, you could suggest that your references are already prepared to receive their call, and oh by the way, here are the people they can get in touch with instead of waiting until the very end before the offer stage. Show vs. tell.

In between your interviews

  • Talk to other employees. Try to have a chat with a current employee, or at least have a conversation over LinkedIn or Twitter DMs. Get the lowdown on what it’s like to work at the company, what they like about it, what they don’t like, etc. Reference it in your discussion with your interview or follow-up email to them. This is a great way to show how you Do Your Own Research.

  • Be available. This goes without saying, but be hyper-responsive, flexible, and available to interview. We have candidates who are totally jazzed to interview on a Sunday morning at 9am or Tuesday night at 9pm and do whatever it takes to make themselves available based on their interviewer’s schedule.

And if you’re working with a recruiter, your availability and responsiveness can actually send a signal as to how serious you are about the opportunity. It’s not necessarily your absolute responsiveness and availability that stands out, but changes in your patterns.

If you suddenly go from hyper-responsive and flexible, e.g. responding to texts within an hour, immediately getting back to requests to debrief over the phone, keeping an open schedule to interview in a lot of time slots over the next few days to not as responsive, then 99.9% of the time you’ve either cooled on the opportunity, are slow-playing our client to wait for other processes to catch up, or are preparing to withdraw from the process entirely, whether it’s based on something within or outside of your control. Good recruiters who keep a very close pulse on candidates who are in a process with their clients will share with them their candidate’s excitement and engagement as well as their potential disengagement along the way. At the end of the day, recruiters are your champion. Give them reasons to remind their clients why you’re a great fit and how excited you are :)

Case study

  • Make sure you understand the requirements, what they’re going to assess, and what they value. This last one is interesting because let’s say you know the founder values curiosity — how can you go one step further and demonstrate that in your case study, whether it be a writing assignment, project plan, presentation, or something else?

If you’re in a process for a Chief of Staff role and made it to the case study, you’ve probably interviewed with a handful of senior or executive leaders on the team already and learned a ton about what they value as a company, and what the founder values as well.

Apply those learnings to your case study. At minimum, that kind of thoughtfulness and attention-to-detail will be the tie-breaker between you and another candidate, and can even put you miles ahead of them.

Offer stage

  • Don’t be afraid to ask for more money. They’re expecting you to negotiate and it might even be a negative signal if you don’t. There is almost always budget to go higher. But be reasonable — both you and your counterparty have to walk away feeling excited and that it’s still a win-win (here’s an extreme example of a candidate who asked for 2.5x comp and still landed the job).

Search Spotlight

Chief of Staff @ Fintech Startup

Our client is a growth-stage fintech startup at the forefront of revolutionizing B2B payments by providing a seamless, integrated approach to the embedded payments ecosystem for business transactions. Their solution integrates into large payment aggregators, accounts payable automation, and procurement software platforms to enable them with a more efficient payment modality.

Role Summary: The Chief of Staff will play a pivotal role in the company, supporting strategic initiatives and operational excellence. They will act as a critical liaison between the executive team and the rest of the company, ensuring effective communication, project management, and alignment with their strategic goals. The ideal candidate is a passionate and energetic individual with a knack for strategic planning, problem-solving, and execution.

Key Responsibilities:

  • Streamline operations and introduce innovative processes to maintain organizational efficiency and alignment.

  • Lead strategic projects and champion change management initiatives.

  • Assist in the development and management of KPIs, delving into data analysis to address and rectify discrepancies.

  • Enhance communication and coordination across departments, ensuring alignment with the company's strategic objectives and operational cadence.

  • Optimize executive organization, preparing the CEO for engagements, managing follow-ups, and coordinating with support staff.

  • Spearhead process innovation, creating foundational practices for business operations, strategic planning, and alignment towards key initiatives.


  • Experience at a high-growth startup in business operations, project management, or related fields

  • Advanced data analysis capabilities and familiarity with tools such as Excel, Google Sheets, and ideally SQL, Tableau, or similar is preferred.

  • Strong understanding of financial principles, strategic planning, and performance metrics.

  • Proficiency with project management tools like Asana, Trello, or Jira.

  • MBA preferred.

What They Offer:

💰 Competitive base salary + equity ⚕️ Medical, dental, and vision insurance 🏖️ Unlimited PTO 📍 This role is 100% remote with a preference for candidates based in EST.

If you're interested and want to learn more about the company, just apply here! I’ll get back to you ASAP if your experience aligns with what they’re looking for.

Know someone who could be a fit for this role? Feel free to share this blog post!

Check out our job board for the full list of opportunities with our clients!

Candidate Close-up

🙋‍♀️ Candidate Background

Key member of the leadership team and thought-partner to the CEO at a hyper-growth DTC products business. Left big-buyout consumer private equity two years ago to pursue her passion of brand-building, helping the company to scale 4x.

This candidate built out and manages 3 separate functions at the company. In her highly cross-functional role, the candidate is central to strategic decision making across the organization.

Key responsibilities & achievements as Chief of Staff to the CEO/Founder include:

  • Equity & Debt Financing: Led and executed Series A fundraise and subsequent debt raise

  • Recruited and manages 3 person Corporate Strategy team; drives data-driven decision making, cross-functional project management, and KPI reporting across the organization

  • Runs Finance function: Partners with external accountants for AP & bookkeeping; Built and owns company operating model and budget

  • Demand & Inventory Forecasting: Built highly sophisticated predictive models that inform inventory purchasing

  • Manages Corporate Admin Function: Legal, insurance, etc. Prior to entering the start-up world, this candidate started her career in consumer-focused IB before joining a $20B+ branded consumer PE fund.

💪🏻 Top 3 Skills

  • Highly thoughtful & strategic approach to decision-making & execution

  • Juggling competing priorities

  • Sophisticated finance acumen & modeling

✨ Proudest Achievement

Taking a career leap - leaving the world of private equity to join an early stage startup - pursuing her passion of building brands.

🔥 What’s Unique

Strong judgement. This candidate knows when to escalate and ask questions, while at the same time independently pushing things forward.

🎯 Career Goals

Build iconic brands alongside high-caliber teammates; always learning along the way. While her nature is to roll-up her sleeves and get in the weeds, she is most excited by driving strategic direction and critical decision making.

Job Opps

🏢 Chief of Staff at Blueground – flexible, furnished apartments for rent

My thoughts: I LOVE this business because I’ve stayed in many long-term AirBnb rentals and some of them seem great but don’t have what you need, e.g. truly high-speed internet, king size beds, functional furniture that’s actually comfortable, fully stocked kitchens, etc. — lots tend to skimp on the nice stuff and opt for Ikea furniture while charging you an arm and a leg. They also tend to lack decent working space or just thoughtfulness around accommodating remote workers.

Blueground champions the concept that you should “feel at home wherever you choose to live” and truly caters to the digital nomad.

The Chief of Staff role at Blueground offers a unique opportunity to work closely with the CEO on pivotal projects, streamlining operations, and ensuring the leadership team operates in harmony.

Ideal candidates will have:

  • 5-7+ YoE in fast-paced environment; candidate archetypes include “The Startup Buff”, “Finance Pro” and “Management Consultant” (Right Hand’s candidate archetypes can be found in this post)

  • Proven ability to manage projects from conception to completion.

  • Strong communication skills, capable of simplifying complex issues.

  • Experience in fostering teamwork and enhancing interdepartmental collaboration.

  • Attention to detail and strategic thinking.

💰 Salary: Unposted but likely north of $175k given the archetypes.

📍 This role is fully remote, with the flexibility to adapt to US time zones and a willingness to travel for team gatherings

📥 Apply here.

🧬 Chief of Staff at GeneDx — genome & exome testing for faster diagnoses

My thoughts: Chief of Staff roles in biotech are pretty rare — they tend to be very senior positions and ideal candidates need to come to the table with a ton of domain expertise and usually combinations of advanced degrees like MBA + MS/PhD or even MD in some cases. The salary ranges match the high expectations around qualifications, and GeneDx is no exception at $260-290k for this role.

Given the above, I must say that I am absolutely shocked that there isn’t a single sentence around desired candidate experience and skills in the JD 😅. Maybe the primary responsibilities and leadership behaviors on the job are meant to double for this section?

I’m going to give the benefit of the doubt here and assume that this is a simple copy/paste error, and that somewhere out there, the list of required and preferred qualifications are floating around!

📍 This role is onsite in San Francisco.

📥 Apply here.

😊 Chief of Staff at Feeling Great — mood boosts within 2 hours

My thoughts: Feeling Great is on a mission that’s close to my heart - improving mental health. They’re mixing tech with some serious psychological expertise to create an AI buddy that boosts your mood in just a couple of hours.

With $6 million in seed funding, they're gearing up to take this app to the next level and they need a Chief of Staff to help smooth operations, lead special projects, and help coordinate the executive team.

Ideal candidates will have 5-7 YoE (and an MBA) and given the focus on strategic planning, project management, and operational rigor, some blend of the “Startup Buff” and “Management Consultant” profile might be a good fit here.

📍 This role is fully remote.

📥 See the JD here and apply by emailing your resume to

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