There are a few key stages of any recruiting process:
- Networking & Applications
- Evaluating Offers
I’ll share a few lessons learned for each stage.
There are a few things you need to prepare to “take yourself to market”:
- Your story
- LinkedIn profile & resume
- Intro blurbs
- Key data points
Your story is composed of answers to a few key questions:
- Who are you professionally?
- What type of expertise do you have?
- How did you get there?
- What type(s) of role are you looking for?
- Why did you / are you leaving your last role?
Who are you professionally?
This is the beginning of your answer to the standard prompt: Tell me about yourself. It should be a very brief executive summary of what defines you as a professional based on your skills and values. It should be:
- Communicated in plain English
- Very short (2-4 sentences)
- Easily understood
Why? When the person leaves the conversation, they will only remember a very short summary of who you are. If you talk for 5 minutes, they will make up their own answer in their mind.
What type of expertise do you have?
This is the follow-up to the prior prompt. Once they understand your archetype as a candidate, they will want to go deeper so they understand how your expertise matches against the jobs they might consider you for.
In the context of a CRO role, folks usually wanted to know my experience across a few dimensions:
- Business size: annual revenue
- Team size: number of FTEs in direct org
- Company ownership: private – VC, private – PE, public
- Functions reporting direct: sales, customer success, revenue operations, marketing
- Customer size: SMB, Enterprise
- Sales cycle
- Annual contract value (ACV)
- Business model: SaaS, marketplace, other
- Company operating point: revenue growth rate, EBITDA %
How did you get there?
The answer to this question is a version of the normal “walk me through your resume” section of an interview.
I would always err on the side of keeping it too short vs. too long. And I think interviewers get the most value from hearing about the transitions. Why did you move from Company A to B? Why did you change roles? Why did you go back to school?
What type of role are you looking for?
There are a few key elements to consider:
- Company size (e.g., $100-500M revenue)
- Role / title (e.g., Director of B2B Marketing)
- Industry (e.g., tech, consumer products, consulting)
- Vertical (e.g., healthcare, insurance, retail)
- Locations you are willing to live (e.g., Boston or New York)
- Collocation approach (i.e., remote, in-office, hybrid)
Why did you / are you leaving your last role?
My big learning is that your answer to this question should be very short. Most people don’t want to go deep on this topic. They just want some high level context. It’s totally fine to say something like: “I really enjoyed the earlier stages of my current company. We’re much bigger now and the challenges are different. I’m hoping to go back to something more entrepreneurial.”
Make it short, honest, and positive about the future.
LinkedIn Profile & Resume
Updating your LinkedIn and resume is a pain! Sadly, my advice is to suck it up and invest whatever time is required to make them great. If you have to prioritize, invest more time in LinkedIn. Everyone will look at it. And it can be an incredible source of leads as it has become a core tool for recruiters across the spectrum of roles.
Here are a few resources I found useful:
- Formula for a Winning Resume: great article I have used for 10+ years
- LinkedIn Guys: free tools to improve LinkedIn and resume
- Jobscan: automated tool to review and edit LinkedIn and resume
- Chat GPT: great at editing / tailoring resume bullet points
My biggest learning was to optimize your LinkedIn profile for SEO. Recruiters search for candidates using keywords. LinkedIn Guys and Jobscan above will help you identify the keywords that are relevant for your search and will suggest places to layer them into your LinkedIn profile.
If you are targeting executive / leadership roles, you will be doing a ton of networking in your search. Write out a few introduction blurbs that you can quickly copy / paste into emails. You will likely need at least two versions:
- For People Introducing Me to Others (Networking)
- For Recruiters
Remember to keep it very short. You only need to pique someone’s interest. If you can’t do that in 3-4 sentences, you either need to re-write them or it likely isn’t a fit.
Key Data Points
When you prepare your resume / LinkedIn profile, you will likely go back through your work over the past few years and will quantify many of your accomplishments. Take an extra step to brainstorm all the likely questions interviewers may ask you about your last 2-3 years and take the time to write down those answers so they are ready to go.
In the context of go-to-market leadership roles, you may need data points such as:
- Revenue by quarter / year
- Revenue growth rate by quarter / year
- Performance vs. quota by quarter / year
- Size of team over time
- Revenue and/or account churn over time
- Monthly / annual employee attrition within your org (if it was large)
- Employee satisfaction score over time
- Customer satisfaction score over time
When you reach the offer stage, many companies will ask you for references. You don’t need them until that stage of your process, but it’s easier to ask for them when you are telling people about your search and re-engaging your personal network.
I got the advice to pull together a list of 5-10 folks who can provide references for you, summarize it in a spreadsheet, and just offer it to anyone who wants a reference for them to pick from.
Networking & Applications
One of my biggest early learnings about my job search was that you don’t apply for C-Suite roles. It is a “networked” search which means that you will source opportunities either through people reaching out to you (mostly after finding you on LinkedIn) or through proactive outreach.
In my process, I proactively reached out to a few groups of contacts:
- Personal Network: I went through my entire list of LinkedIn connections and reached out to a ton of friends, former colleagues, and acquaintances to catch-up. I got to hear how they were doing, reinforce our connection for the long-term, and often they knew someone else who could help me in the search and would do a warm intro.
- Headhunters: I reached back out to all recruiters who had contacted me in the past to reconnect. And I did research to identify the large recruiting firms that I wasn’t connected with. And I used a combination of cold outreach and personal connections to close those gaps.
- Private Equity Firms: Over time, I created a list of PE firms which invested in the size of companies I was targeting. Then I used my personal network to try to get introductions to the firm. Most firms have a dedicated talent lead who will help place executives in their portfolio companies.
- Venture Capital Firms: Similar to the PE firms, I built out a list of VCs which might be a good fit for my target company size.
- Hiring Companies: I used my personal network and some online research to identify high potential companies that might fit my target criteria. This works best when a candidate has specific expertise, wants to apply it in their next role, and is geographically flexible.
I used a simple Google Sheet to track my progress on outreach. I kept it up to date as I moved through the process with each contact. There wasn’t a lot of magic to my approach. It’s just about using a process that works for you. The columns in my sheet were:
- Name (of contact)
- Contact type (e.g., personal network, headhunter, hiring company)
- Last step
- Next step
- Role (that they are hiring for)
- Company (that the role is for)
- Write down your prep: Create a document and write down your answers to the most common questions (below). After you have done a few interviews, go back and improve your answers based on your learnings.
- Tell me about yourself
- Tell me about your role / team and the business at your current company
- What is your leadership style? Management style?
- What are you most proud of (3+ stories)?
- What are mistakes you learned from (3+ stories)?
- Tell me about the sales process in your last role
- How do you inspire your team? Hold them accountable?
- How would others describe you?
- Bomb a few interviews: I got a lot of advice to do mock interviews. That is a great idea! Additionally, you can do a few interviews that are unlikely to lead to a great fit. Those can give you the jolt of motivation required to tighten up your pitch. You can also make a few mistakes that you can avoid in the higher stakes interviews.
- Spread out phone screens: The most common conversation outside of your personal network will be a phone screen with a recruiter. These can get tiring because they are pretty repetitive. You answer the same questions each time while the recruiter tries to figure out if you fit the basic criteria to have a first round interview. I recommend spreading them out so that you can always engage with great energy. Don’t do a ton of them back-to-back.
- Use AI tools: Chat GPT was an incredible resource when researching companies, new industries, preparing for interviews, and working on take-home assignments.
- Know What Matters Most: There is an almost infinite list of factors to optimize for when considering a new role. Company size, strength of the product, belief in the mission, company culture, leadership team, challenge of the role, ability to do the role, compensation, location, and much more. Write down the 3-5 key factors for you and revisit it regularly. By the time you get an offer, you should have a really good idea of whether you are likely to take it.
- Do Your Diligence: As you head towards the offer stage, you should ramp up your diligence on the company. Personally, I like to talk to customers of the company so I can hear what they think about the product. This is more doable in B2C or SMB B2B businesses, but can be done at the Enterprise level. You can even ask the hiring company to help you as it will set you apart as a candidate. Another form of diligence is “back-door” references. Ideally, you want to find some ex-employees to talk to who will offer you an unvarnished view of the company’s strengths and weaknesses.
- Compensation: Avoid sharing your target compensation. Recruiters will often ask you so they aren’t wasting time on either end. However, the reality is that every role has a rough budget. If they want to ensure no one’s time is wasted, they can share the budget with you and you can react to it. If not, you can just wait until the offer stage and negotiate. In the meantime, you can do research on the side to determine whether it is unlikely that they will offer you less than you are willing to accept.