Mastering the Market: Insider Tips for a Successful Job Hunt
This job hunting post is a guide for all those seeking employment in a challenging market. May you swiftly find your next opportunity.
If you've recently lost your job, take time to decompress first. Avoid rushing into another position immediately. You've earned a break after operating at full capacity for an extended period of time. Once you embark on your new challenge, there won't be an opportunity for a break. I experienced a hiatus between jobs after a non-stop 24-year career, the last 18 years as a product leader. Taking this break was eye opening—it allowed me to pursue my passions and consider turning them into a viable career.
In job searching, I've learned to treat myself as a "product" and apply strategies similar to those used by startups to generate awareness and market myself (highlighting the value proposition and differentiating factors). As a product management leader, I appreciate this approach and have successfully used it to pinpoint the right job opportunities. For instance, I positioned myself as specializing in B2B SaaS workflow-based productivity tools with three core value propositions:
Implementing Product-Led Growth (PLG): Introducing strategies to enhance product acquisition, monetization, and retention.
Reinvigorating the Voice of the Customer: Addressing the disconnect in customer feedback during product development to boost adoption and loyalty.
Driving Rapid Strategic Growth: Advancing business growth through frequent, strategically aligned product releases focusing on customer impact.
I also emphasized domain expertise to refine further my audience targeting. For example, I frequently targeted companies building solutions for developers to align with my background in Developer Tooling. In the 2023 job market, many employers prioritized a strong domain fit, and my shorter engagements in Cyber Security and EdTech didn't quite match up to those with deep expertise in these fields.
One candidate I encountered aptly noted that employers are more inclined to seek Skills than raw Talent in today’s market.
The following checklist may appear extensive, and it is—because job hunting is a full-time job. I allocated 50% of my time to the job search. The remainder I invested in up-skilling, engaging in business projects, and giving back to the community, activities that included:
Mentoring SaaS startup founders, from Seed to Series A stages, to help them navigate a challenging tech market.
Imparting my job-hunting expertise to over 40 job seekers in online Zoom sessions.
Honing my design and coding skills and studying machine learning to stay abreast of the latest trends.
Participating in the Hogan Lovells 2023 M&A Boot Camp to enhance my suitability for executive roles.
Attending industry events such as TechCrunch Disrupt and Figma Config 2023.
Starting a formal blog, Quantified Product, and an online agency, Next Outcome.
Establishing an LLC for my son's e-commerce business, ensuring proper business operations for dropshipping.
This comprehensive approach to job hunting will not only prepare you for your next role but, I hope, will also enrich your professional and personal life.
Prepare for the job search:
[ ] Read the book Never Search Alone
[ ] For a structured job search approach, consider The 2-Hour Job Search and The Job Closer by Steve Dalton
Although Steve Dalton's examples often target college graduates, they also apply to mid-career and senior professionals. His books stand out for their systematic methods, which may resonate differently with each reader. These methods gave me clear directions when I was at a standstill and advocated for a rapid approach to networking—a central theme in Steve’s strategy.
Don't search alone
[ ] Join a Job Search Council to support you during the search or a community like Rands Leadership Slack. Both are free to join.
Engage with a support group for motivation and encouragement, and to widen your network. Adopt Phyl Terry's Never Search Alone method by becoming part of a Job Search Council. This service is complimentary, and the team will pair you with fellow job seekers who have similar career ambitions and backgrounds. Within this group, you will follow a structured process that includes gathering feedback from past supervisors and colleagues, crafting a "candidate market fit" document, refreshing your LinkedIn profile and resume, and networking to broaden your reach.
Embrace the startup mindset: be innovative, resourceful, and think unconventionally to open new doors. Read The Startup of You by Reid Hoffman. Despite sometimes seeming like an advertorial for LinkedIn, this short book underscores the importance of adaptability and networking in modern career trajectories.
The Rands Leadership Slack is another excellent community with a supportive environment where job seekers share advice and interview experiences.
[ ] Speak with your former managers, colleagues, and direct reports. Learn about your strengths and the memorable outcomes that you achieved for the business. This reflection will help you target your job search based on your strengths.
[ ] Draft a one to two-page document outlining your unique value proposition and job aspirations, to update your LinkedIn profile and resume with your strengths and objectives. The document will serve as a baseline for discussions and to clarify your job search intentions.
[ ] Craft a concise tagline that encapsulates what you are seeking. For instance, my tagline guided discussions with recruiters and network contacts toward B2B SaaS:
Seeking a product leadership role (Chief Product Officer / Head of Product) at a high-growth B2B SaaS company with a strong social mission.
[ ] Update your resume with insights gathered about yourself:
Ensure your full name is included and searchable on LinkedIn.
State the tenure with month and year (e.g., July 2022 - July 2023).
Describe each company and its industry concisely to showcase industry experience.
Specify the tools you utilized to achieve your goals (e.g., "Used tool X to accomplish Y").
Detail the outcomes and key performance indicators (KPIs) that you impacted at the business with each achievement.
[ ] Update your LinkedIn profile with insights from your self-research
Craft a compelling headline (located under your photo) that encapsulates your career highlights and what you seek, designed to grab attention and prompt further reading. View my LinkedIn Profile as an example.
Upload a professional photo (not a family photo or cartoon).
Prominently showcase your value proposition in the About section.
For each role, include relevant skills. You may expedite the selection process by clicking “+ Add skill,” typing a vowel (a, e, i, o, u), and selecting all pertinent skills to avoid searching for each one.
Attach relevant media to each professional role, such as webcasts, podcasts, or blog posts, by linking them directly to the corresponding job entry.
Standardize your job titles across recent positions. Match the job titles to those currently used by employers. For consistency, if you have been a Product Manager in your last three positions, label them accordingly, even if your employers had variations of the title. A coherent career trajectory can make your resume more appealing.
[ ] Establish your brand with a personal website. For example: About Filip.
In outreach emails for potential job opportunities, include an “About Me” link in your signature, which had the highest open rate for me, even surpassing LinkedIn. Also, link to your newsletter (e.g., Quantified Product) and Twitter profile (e.g., Filip's Twitter) to demonstrate an extensive social media presence.
Create an online presence easily with website builders like Wix or choose one of the many free Wordpress hosting providers like Wordpress.com or a more premium hosting provider like Kinsta. Leverage one of the website themes to speed up the site creation process. If you have some technical chops, you can build your website from scratch with a low-code builder like Webflow, which I have used for my About Filip page and my NextOutcome business website to solicit work.
Filip's Daily Routine:
[ ] Organize your day to maintain discipline and prevent burnout during a 4-hour daily job search.
To avoid an inefficient day, start with a healthy morning routine and group similar tasks together, such as job applications, which should only take up part of the day.
My schedule was as follows:
Woke up at 5:45 am, prepared for the day, and went to the local gym for a morning workout until 7:30 am.
Dedicated time to applying for jobs, blogging, and networking from 8 am to 12 pm.
Allocated time for learning and skill development from 12 pm to 2 pm.
Worked on my Next Outcome business from 2 pm to 5 pm.
Every Friday afternoon, I assisted other job seekers by sharing my workflow in 20-minute meetings and encouraged their job pursuits.
Maintaining a healthy mindset is crucial, especially on challenging days. I engaged with books on confidence, mental toughness, and discipline, including:
The Confident Mind by Nate Zinsser.
12 Rules for Life: An Antidote to Chaos by Jordan B. Peterson.
The Manual: A Philosopher’s Guide to Life by Epictetus.
Job Search Activities:
[ ] Activate your network, as most jobs are discovered through connections.
Networking is critical in job searching; become proficient at it. Explore Chris Fralic's insights on networking through his blog post: How to Become Insanely Well-Connected.
Draw inspiration from Steve Jobs on YouTube about asking for help. Fear of failure can impede progress.
As previously mentioned, The 2-Hour Job Search by Steve Dalton provides a step-by-step networking strategy for those who need guidance.
[ ] Attend meetups, conferences, and join platforms like Lunchclub to meet potential job search allies (my meetups led to consulting insights and even CEO interactions, including a consultation with one CEO I met through Lunchclub).
[ ] To warm up your network, post engaging content on LinkedIn AT LEAST WEEKLY—ideally multiple times per week due to limited initial reach. For content ideas, visit my LinkedIn Activities.
Regularly write blog articles based on interview topics or common industry challenges and share them across your social channels.
Share your articles after networking conversations by sending follow-up thank-you notes with links. My blog, Quantified Product, is hosted on Substack for easy distribution. Alternatively, consider platforms like Wix, as demonstrated by Dimitris Adamidis on his Rev Ops Venture site.
BONUS: With frequent posting and a significant follower count, enable “Creator mode” on LinkedIn to amplify your posts and encourage following.
[ ] Set job alerts on primary job boards like LinkedIn.
[ ] When applying, tailor your resume's job experience headline to match the employer's requirements in the job description. The headline customization can significantly improve the chances of your resume being noticed. I also maintained two versions of my resume, one for "Head of Product" and another for "VP of Product", with the former geared more toward a first product leadership hire.
Whenever I was referred to a hiring manager or recruiting team, I customized my resume further, incorporating language from the job description to bolster my candidacy. However, I reserved this level of tailoring for positions with a personal advocate or for opportunities I was particularly interested in, as it can be time-consuming. I also ensured that my resume contained many keywords from the job description, for which ChatGPT was incredibly useful at pointing out.
Due to high competition, I avoided "Easy Apply" listings. I applied directly on the company's website instead.
If ChatGPT isn't part of your toolkit, you can use Jobscan—a tool that can help you identify which aspects of your resume to customize for a better chance of eliciting a response from employers.
[ ] Email hiring managers or company leaders to showcase your employment credentials. This approach often yields better results with smaller companies, but it's worth attempting with larger organizations too.
Upon finding a desirable job, take the time to research the hiring manager and any pertinent leaders. Engage with them on social media, ensuring your interactions are relevant and thoughtful. For instance, contribute meaningful comments on their recent LinkedIn or Twitter posts. If you engage in conversation, your name will become top of mind within 1-2 weeks of engagement.
Subsequently, reach out via email to capture their interest—having interacted on social media will increase your chances of receiving a reply. Begin by contacting senior-level individuals, as doing so draws attention and simplifies the process of deducing their contact details. For example, if you're seeking a position in product management, search for the company on LinkedIn, navigate to the 'people' tab, and filter by “product management” to identify VPs and Directors. The company's website often lists its senior team, providing insight into the CEO and leadership structure. When crafting your message to these executives, weave a narrative expressing a willingness to learn about their business or assertively state why you are the ideal candidate, depending on the approach you find most appropriate for the person you are contacting. Mirror the language of the job description in your email's subject line and body to underscore your suitability for the role.
[ ] As the skilled marketer you are, you're undoubtedly tracking who opens your emails and whether they've been forwarded among colleagues—a positive indication of interest. It's normal not to receive a reply on your first attempt; this is a common experience for many, including myself. Depending on your initial email engagement level, plan to follow up periodically, spacing out your emails by a few days to maintain contact without overwhelming the recipient.
You should be tracking email opens and frequency. I used a product called MixMax. I had the free plan for 100 emails tracked per month - I used Gmail only for job outreach to maximize the 100 tracked emails and Safari for regular emails where the MixMax plugin didn't work.
[ ] Leverage tools to streamline your interactions with recruiters and simplify scheduling:
Scheduling meetings should be straightforward, eliminating the need for extensive back-and-forth. Use scheduling tools like Calendly when networking, meeting with recruiters, or setting interview times to display your availability transparently. This consideration respects the other party's time and effort in connecting with you.
Integrate your scheduling tool with a video conferencing platform. I prefer Zoom and have invested in a subscription to facilitate unrestricted group calls when necessary. Google Meet and MS Teams are also viable options. Linking these tools will automate the meeting setup process.
[ ] To truly stand out, consider sending a video message instead of an email when a significant impact is necessary. I use VideoAsk for this purpose.
Your Setup
[ ] Ensure your microphone and video setup are above average; first impressions are critical.
A strong first impression is essential. The HBR Article, "How to Make a Great First Impression", effectively summarizes its importance. Yet, what is less often addressed in the context of remote interviewing is your computer setup, which equates to your business attire in an in-person interview. It's important to present yourself as well as possible online. Starting a conversation with subpar audio and video quality puts you at a disadvantage, so it's worth investing in a better setup if yours fails to meet the mark.
The clarity of your audio is paramount. I suggest purchasing a dedicated microphone if your audio quality differs from that of professional YouTubers or podcasters.
I recommend the Shure MV7 microphone with a boom arm.
I use the Shure SM7B microphone, which requires an audio interface with XLR input, such as the RME Babyface Pro FS. This setup is more complex and costly, so I recommend it only if you aim for professional-level audio for projects like podcasting or film production.
Avoid using a fake background in your video. In a class on online meetings, I learned that a virtual background can subconsciously signal to others that you might be concealing something, undermining your authenticity. Whenever I encounter someone using a virtual background, I instinctively wonder if they are hiding something. If you have a dedicated space for your meetings, creatively decorate your real background.
Be mindful of overly bright backgrounds, such as windows or lamps, as they can cause your face to appear dark when the camera auto-adjusts for the bright light.
If your room's lighting is poor, consider purchasing an affordable LED light to illuminate your face. A light is beneficial because most built-in computer cameras perform poorly in low light, resulting in a dark and grainy image. A dedicated light source is a cost-effective alternative to investing in an expensive camera to improve lighting conditions.
Learning opportunities
[ ] Continue to enhance your knowledge within your field of expertise while job hunting, staying abreast of current trends to inform your discussions.
Engage with literature, including books on personal development and those specific to your domain. For me, it was Python programming and AI.
Participate in meetups and conferences. For instance, I have attended events focused on product management, engineering, and AI, including Config2023 by Figma and TechCrunch Disrupt.
Join online webinars. I've participated in venture capital webinars to gain insights into the startup ecosystem and understand current needs within the startup space.
Enroll in courses to update and expand your skill set. I have completed product management, AI, and mergers and acquisitions courses to ensure my skills remain current.
Job Interviews:
[ ] Recalling and articulating your accomplishments in a compelling way can be challenging, especially if you've been out of work for some time. Detail 3-5 projects you've worked on in recent years, which you also included in your resume. Document every detail you can recall so you can review and refresh your memory before an interview, allowing you to draw on these projects as examples. For further information, visit the blog post The "How" Part: Walk Down Memory Lane.
Framework to help you recollect project details
The strategic driving factors for the project - unlocking TAM, opening new markets, improving COGS, driving user success, other?
How you got involved - did you come up with the project? Get tapped on the shoulder? Pick it up when it was a flaming hot mess?
Who was involved - leaders, stakeholders, customers, core team members?
Success criteria - how was success defined? This is a great time to establish how impossibly complex the project was (which sets you up to be the hero in your stories)
Why it was complex - new tech? huge scope? tight timeline? massive team? powerful stakeholders? major financial impact?
What you did to drive success - specific actions you took.
Issues that came up - people, tech, implementation, partners, infra, etc.
Conflict that arose - executive sponsors, team members, your boss?
The ultimate result - this should include final outcomes for the stated success criteria as well as longer-term success and strategic / business impac t.
What you learned - what you learned along the way.
How you have grown - how did you become a better professional and how did you implement these learnings since then.
[ ] For certain positions, presenting a playbook to the hiring manager can be advantageous—for instance, an account executive's 90-day ramp-up plan. While sharing detailed plans in the initial stages may not be feasible due to unknown challenges, I advise you to do so after several interviews have provided you with strategic insights and a better understanding of the role. For example, I compiled a product strategy following discussions with a hiring manager, which entailed over a dozen hours of research. This effort proved worthwhile, as evidenced by the hiring manager reviewing the document 13 times, including four times on the eve of their final meeting with the leadership team to decide on the hiring.
[ ] Master the STAR framework to answer behavioral interview questions effectively. Aim to showcase every facet of your success, from a high-level strategic perspective on the project to detailed, hands-on execution that proves your capability. For a more in-depth explanation, refer to the blog post Learn the Behavioral Frameworks and Never Again Sweat an Interview Question.
STAR Framework
S: Situation - what was happening at the time (context)
T: Tasks - what you were responsible for
A: Action - what you did to solve the problem and deliver outcomes
R: Result - the impact of your actions
Bonus time permitting:
Share what you learned
Share how you’ve adopted your approach for future projects
Make thank you notes a habit
[ ] I make it a habit to send a thank-you note after every interview. If you're uncertain about the email address, don't hesitate to request it at the end of the interview—I usually do. The thank-you note should be customized to reflect the conversation, including references to topics discussed. As previously mentioned, I monitor my emails with MixMax to gauge engagement. Typically, interviewers open my email multiple times.
Example thank you note from my interviews
Frequently, I raise the topic of books in an interview with the titles that align to the conversation to create engagement and value for the interviewer. If it’s product management practices, for example, I share that I’ve read and follow best practices similar to Marty Cagan’s, which were outlined in his books Inspired and Empowered. This is how my email looks like as an example:
Thank you for taking time to meet with me. I enjoyed our conversation and it was great to connect virtually. Per our conversation, besides my blogs, you can get a sense of my product leadership philosophy in the following books, which I use to mentor the team:
Inspired: How to Create Tech Products Customers Love by Marty Cagan
This book is mandatory product management reading for my team. It's a comprehensive book on what good product management looks like including roadmaps, objectives, product discovery, planning, ideation, prototyping, and much more. As it doesn't get enough into the "how to", I subscribe the team to the Reforge program to develop product management skills.
Empowered: Ordinary People, Extraordinary Products by Marty Cagan
This book is great product leadership reading. Coaching, staffing, product vision/strategy, collaboration, team topology, and setting objectives. All fundamentals of a great product leader.
Continuous Discovery Habits: Discover Products That Create Customer Value and Business Value by Teresa Torres
When I joined my last employer, I noticed that product/design/engineering was relying too heavily on product usage data and didn't speak to / do research with actual customers. This is how I grew up in product management - speaking with customers and finding patterns to identify opportunities/pains to solve. The book outlines a nice technique for mapping opportunity space, prioritizing opportunities, and discovering the solutions as a team (product manager, designer, and tech lead).
I look forward to continuing our conversation,
Preparing for Your New Job:
Before taking on the new role, my first step was to thank everyone in my network who supported me in my job search with an email or message on LinkedIn. I described my journey in finding the role and what I would do at the job. It's essential to recognize your network's contribution in helping you find a job and continue to stay in touch.
Learn how to navigate your first 90 days effectively by reading The First 90 Days.
Enroll in Victor Cho’s complimentary career development course to become more efficient at work and advance your career: Victor Cho’s Course.
Additional Resources:
Learn how to excel in any first-round interview with guidance from coach Erika: How to Pass Any First Round Interview.
Consider exploring the transformative career change journey with Working Identity: Unconventional Strategies for Reinventing Your Career by Herminia Ibarra.
Read Designing Your Life: How to Build a Well-Lived, Joyful Life by Bill Burnett and Dave Evans to discover how design thinking can help you create a fulfilling career and life.
Discover who can help you land your next job according to LinkedIn data: LinkedIn Data on Job Assistance.
Draw inspiration on achieving success from Sam Altman: How To Be Successful - Sam Altman.
Explore a productivity hack involving ditching to-do lists for calendar scheduling with insights from Sam Corcos on The Tim Ferriss Show: Calendar Scheduling System.
Learn how to efficiently use Gmail with this guide to achieving inbox zero: Inbox Zero Setup for Gmail.
I utilize the Things 3 app on my Mac to keep track of follow-ups: Things 3 App.