Tag: job hunting

The CTO’s Guide to Crafting a Technology Leadership Resume

Crafting a resume as a technology leader is about more than listing roles—it’s about showcasing achievements, leadership, and strategic impact. Learn how to tailor your resume, highlight cross-disciplinary management, and leverage tools like LinkedIn and personal websites to stand out for executive roles.

A common discussion with people I mentor is how to properly structure a resume or Curriculum Vitae. It comes up often enough that I felt compelled to write about it last year: “Sweat the details on your resume, especially if you are a developer or technology leader.” In the last few weeks, I have reviewed multiple resumes from folks hoping to achieve a director-level or above role. I wanted to share some lessons on how an executive-level resume differs from others in Technology.

As a technology executive, your resume is your calling card—a teaser trailer for your professional achievements. Crafting a resume that highlights your leadership journey while demonstrating value is an art form, particularly as you aim for senior roles like VP, CTO, or similar. Here are key takeaways and strategies to ensure your resume stands out.

Tailor Your Resume for the Role

Your resume isn’t a one-size-fits-all document. Different audiences—recruiters, hiring managers, or automated systems—expect varying levels of detail. To make a strong impression:

  • Create multiple versions of your resume:
    • Short-form (2 pages or less): Use this for recruiters or direct submissions. Focus on succinct highlights that convey your biggest achievements and relevant experience.
    • Comprehensive (full-length): Maintain this detailed record for Applicant Tracking Systems (ATS) or contexts where exhaustive experience matters, such as certain consulting or academic roles.
  • Use strategic brevity: Each version should prioritize accomplishments and impact over exhaustive lists of tasks or skills. At the bottom of the short-form resume, include a URL to your full-length resume, LinkedIn profile, or personal website for those who want more detail.
  • Tailor content to the role: If applying to a startup, focus on entrepreneurial accomplishments. For a multinational corporation, emphasize experience working with large teams or global operations.

Focus on Achievements, Not Responsibilities

Leadership resumes should emphasize measurable outcomes rather than generic responsibilities. This allows you to demonstrate value and differentiate yourself from other candidates. Consider these approaches:

  • Use metrics whenever possible: Quantify your achievements to provide concrete proof of your impact. For example:
    • Replace “Managed a team of data scientists” with “Grew a data science team from 5 to 20 members, delivering a 10x cost efficiency improvement in critical business processes.”
    • Instead of “Improved system performance,” say, “Increased platform uptime from 97% to 99.9% while reducing hosting costs by $500,000 annually.”
  • Highlight transformative initiatives: If you drove major changes—like adopting a new technology stack or transitioning a team to a new operating model—emphasize these innovations and their outcomes.
  • Demonstrate multi-disciplinary management: Showcase examples where you’ve managed diverse teams or disciplines, such as engineering, product, and design. For example, “Led cross-functional teams spanning software development, UX design, and data analytics to deliver a platform used by over 10 million users.”

Put Your Most Recent Role First

Your current or most recent position carries the most weight. It’s likely the first thing a recruiter or hiring manager will read, so ensure it captures attention:

  • Make it prominent: Place this role on the first page and dedicate the most space to it.
  • Emphasize scope and results: Clearly articulate the scale of your responsibilities, such as budget size, team size, and direct impact on the company.
  • Focus on strategic leadership: Highlight initiatives you spearheaded and the outcomes they achieved, particularly those demonstrating thought leadership, cross-functional collaboration, or innovation.

Save earlier roles for subsequent pages, reducing detail as you go further back in time. Roles older than 10 years may only need a line or two unless they’re particularly relevant.

Position Skills Strategically

Technical skills are critical, but how you present them matters:

  • Avoid generic lists: Instead of placing a large block of skills at the top, embed them within descriptions of your achievements. For example:
    • “Led migration to AWS Cloud, saving $1.2M annually and achieving 99.9% uptime.”
  • Highlight relevant expertise: Tailor the skills you emphasize to the role you’re applying for. If you’re aiming for a director role in AI, showcase experiences involving ML frameworks and tools like TensorFlow or PyTorch.
  • Subtly include soft skills: While technical skills are important, leadership roles often require strong interpersonal and strategic abilities. Show how you led teams, resolved conflicts, or drove cross-departmental alignment.

Summarize Career Progression

Rapid promotions and career growth can be a powerful selling point, but they need to be presented succinctly:

  • Highlight trajectory: For example, “Promoted from Senior Machine Learning Engineer to Head of AI within three years.”
  • Simplify titles: If your roles had incremental changes, summarize them into a cohesive narrative. For example: “Advanced from Senior Engineer to Director of Engineering over six years, culminating in leading a 50-person team and delivering $20M in annual revenue growth.”
  • Emphasize leadership: Show how your roles evolved to include greater responsibility, larger teams, or more strategic initiatives.

Cut the Fluff

Hiring managers and recruiters skim resumes. Get to the point by removing irrelevant or overly detailed information. This will make your resume more focused and efficient, ensuring that only the most important details are highlighted.

  • Avoid generic claims: Statements like “Proven leader” or “Results-oriented professional” don’t add value. Instead, provide examples that demonstrate these qualities.
  • Skip common experiences: Transitioning to remote work during COVID-19 isn’t unique. Focus on outcomes that set you apart.
  • Reduce early-career details: Unless highly relevant, roles from over 10 years ago should only include titles and dates.

Use LinkedIn and a Personal Website for Depth

Your LinkedIn profile and personal website can complement your resumé by providing additional details and ensuring you’re findable by recruiters:

  • LinkedIn:
    • Include all positions and significant accomplishments.
    • Add media or links to showcase notable projects, talks, or publications.
    • Use keywords strategically to improve searchability for specific roles.
  • Personal website:
    • A personal website can be a dynamic portfolio, host your detailed resume, and provide links to your projects, publications, or conference talks.
    • Organize your website by sections, such as Leadership Roles, Key Achievements, and Speaking Engagements, to make it easy for recruiters to navigate.
    • Use your website to expand on areas that wouldn’t fit in a resume or LinkedIn profile, like detailed case studies or thought leadership pieces.

Think Like a Hiring Manager

Your resume should:

  • Reflect strategic thinking: Tailor information to the audience and highlight your ability to align your work with organizational goals. This approach will make your resume more strategic and thoughtful, resonating with the hiring manager’s perspective.
  • Demonstrate leadership: Showcase your leadership skills by using examples of team management, cross-functional collaboration, or strategic initiatives. This will make your resume more confident and assertive and reflect your leadership potential.
  • Inspire curiosity: Provide just enough detail to make recruiters and hiring managers want to know more about you.

Remember, the goal of your resume is to secure a conversation—not to answer every question upfront.

Advice for Aspiring Executives: Breaking Into Leadership Roles

If you’re seeking your first executive-level (Director or above) role, your resume needs to convey readiness and potential:

  • Reframe your achievements: Highlight instances where you took on responsibilities beyond your official role, such as:
    • Leading cross-functional initiatives.
    • Mentoring junior staff or peers.
    • Driving strategy or innovation.
  • Show leadership impact: Even if your title doesn’t reflect it, focus on achievements that demonstrate leadership qualities, such as:
    • “Initiated and led a company-wide migration to DevOps practices, reducing deployment time by 80%.”
    • “Mentored three engineers who were later promoted to senior positions.”
  • Emphasize thought leadership: Include speaking engagements, publications, or significant contributions to open-source projects to showcase your influence in the field.
  • Network strategically: Your resume is only part of the equation. Attend industry events, contribute to discussions on platforms like LinkedIn, and seek mentorship from executives who can provide guidance and referrals.
  • Communicate readiness in your summary: Begin your resume with a compelling summary that positions you as an emerging leader. For example:
    • “Engineering Manager with a proven track record of driving strategic initiatives and leading high-performing teams, seeking a Director role to deliver innovative solutions at scale.”

Breaking into executive roles requires showcasing your potential and articulating how your experience aligns with leadership expectations. By tailoring your resume and approach, you can make the leap into senior management.

By taking a strategic, minimalist approach to your resume, you’ll showcase your accomplishments and demonstrate your ability to communicate effectively—a critical skill for any technology leader.

Interviewing your prospective employer

Not long ago, I was mentoring someone starting a search for a new role. The person was curious about how to interview a prospective employer.

image of a meeting from https://www.cira.ca/stock-images/gallery

Not long ago, I was mentoring someone starting a search for a new role. The person was curious about how to interview a prospective employer. I wrote explicitly about this in a blog post a few years ago (https://leaddev.com/professional-development/taking-thoughtful-approach-job-search-process), but I think I was able to further distill some of the ideas in our conversation.

There are three things when considering a new role assuming the basics (i.e., pay, benefits, location) make sense.

  1. Can you be successful at the company?
  2. Does the role move you toward your career objectives?
  3. Are you excited about what you will work on?

Suppose you can get all three. Wow! Take that job! Two of the three is pretty good, but it likely means that you should not expect the role to be long-term unless you misjudge the situation or something changes. One of three? Take it if you must but have an exit plan.

If you are in a decent role today, you can always choose to keep looking rather than take something that doesn’t meet enough of your criteria. While the lure of something new might be tempting, it can be hard to understand a role before you are established in it. If your initial investigation raises questions, it may be better to keep your search going.

The critical element is knowing yourself and the perspective role well enough to make the determination (the technique I describe in the blog post referenced above is helpful for this). If you don’t know what you want, keep exploring. Look to new roles to increase your skills or experience with industries, company size, or company culture.

Once you know the conditions where you do your best work, where you want to go with your career, and what excites you to work every day, you can put together questions to ask when talking to the recruiter or as part of the interview process.

Try to avoid asking direct, obvious questions. If the interviews are going well, people may tell you what you want to hear. For example, asking, “How is the work/life balance at your company?” is less likely to be helpful than asking, “What times do meetings usually start or end during your day?” If several employees tell you that their day starts early or ends late, you will see some work/life balance patterns.

Another problem with direct questions is that they reveal more about you than you might want in an interview. For example, when a candidate asks me a direct question about something specific, such as raises, review processes, or work/life balance, it tells me not just that they are interested but that they may have had bad experiences with this in the past. If I get a sense of a bad experience, it will usually prompt me to better understand the nature of their concerns. If you are concerned about review processes, for example, I wonder if you have received negative reviews in the past and what was the story behind them. So, asking more generally about how often the company performs appraisals and the process will elicit less concern than asking how employees can appeal negative reviews.

Ask indirect questions about how the work is done, the day-to-day responsibilities of the role, and what conflicts arise. Look for clues in the answers that speak to reality. You may find some of your interviewers are more forthcoming and open. Leverage that transparency. Find friends or friends-of-friends that know people who work there to get the unvarnished truth.

But also realize that companies evolve just as people do, just as you will. So even if things are good for you initially, they may not stay that way.

So, when your three-of-three company becomes your two-of-three company, you may wait things out to see if things will change, but you also might want to start looking for your next three-of-three company. Although every company will have good/bad periods, once you have been at a company for a while, you’ll understand if the current situation is temporary or part of a more permanent shift.

Of course, in today’s job climate, you might need to take that one-of-three job or even zero-of-three position. If that is the case, don’t despair. Instead, focus on taking care of things until you can find a role that fits you better. Tech is cyclical, just like the broader economy. If you can wait it out, things will get better.

Living in an Employer’s Market as a Developer

The great thing about being in technology is that it is a growing field. There are tons of jobs, and companies are always complaining about how hard it is to find talent.

That is until it isn’t.

It isn’t clear what will happen during this pandemic, but the layoffs and hiring slowdowns or pauses have started.

Many developers have never known a time when companies were not clamoring for their services and bidding against each other.

Having my startup go bust in the dot-com bubble bursting of 2000-2001 and having seen what employment options were like in 2008-2009, I thought I could give some advice to those of you who may be in brand new territory.

If you find yourself unemployed during a bust, you will need to change your tactics. You may be used to an employee’s market, but you are entering an employer’s market. Companies will suddenly find many options for their roles—very qualified, even overqualified, folks who are willing to take a lower salary for their positions. Jobs you wouldn’t have considered previously are no longer returning your e-mails. They can find people better than you cheaper.

Even if you currently have a good job, the security of that role may not be what you expected. Be prepared.

Save your money

If you live somewhere expensive, the rent and other prices are likely to go down more slowly than salaries. You need to start cutting your expenses and build up a cash reserve.

Hopefully, you already have a few months of money put aside somewhere other than the stock market. In a crash, selling your investments in the dip is the last resort. If you don’t have that cash reserve, start building it now.

Stop unnecessary purchases: buy groceries instead of door-dashing meals, take public transportation instead of Lyft, do your laundry instead of sending it out. This is the way that most people live.

You will be surprised how much money you can save by making a few changes. Once you have your reserve (enough to live on with a reduced, reasonable, lifestyle for a few months), you can go back to your spending patterns, or continue to build your savings (which is smarter). During the previous busts, very good, very senior developers ended up unemployed for many months.

Stay Positive

I left a good job at Microsoft to join a startup in 1999. That startup crashed a few months later. After trying to help the leadership revive it for a few months, I joined a friend in building a new startup. We had some angel money, but I was paying the rent and some of the other bills myself sometimes. We were ready to go out for our first real round of funding in September of 2001.

After 9/11, what was left of the investment and job market completely fell apart. We could not raise money. After a few months of trying to keep things going, I needed to start earning a paycheck again. I was selling my stock to pay the bills, and those shares were now worth half of it they had been before.

I assumed it would be easy to find a job. It always had been.

Jobs were suddenly scarce.

I found myself applying blindly to companies that I would never have considered before. Few replied.

Weeks turned into months. I started to lose faith. Occasionally, I would get an actual interview. But by then, the fire had gone out in my eyes. I was passed over for roles that required way less experience than I had. I had lost my confidence, and it showed in interviews.

Eventually, through a friend, I was able to land a contracting job, back at Microsoft. It was a bit humiliating, but I was happy to be working and earning again.

I later found out that I was one of the last people to get that level of contract. The contracting company realized that it could hire people of my seniority at lower contract rates.

Working again gave me my confidence back. I did well and got converted back into a full-time role. When I did, though, my manager negotiated my salary down. I had to take a serious pay cut. I had no choice, and he knew it. I took the job.

Now, as an employee again, I was on interview loops. I spoke to many good developers who were in the same situation I had just left. They had lost their confidence, just like I had. Their answers to questions were non-committal. They were tentative. They were so used to being rejected that it made it hard to approve them.

If you find yourself in that situation, you need to do your absolute utmost to project a positive aspect and some self-confidence in your discussions with recruiters and employers. Even if you have to fake it. Displaying confidence will make a substantial difference in how you interview.

Some money is better than none

If you get an offer, it may be well for a lot less than you expect. You may need to take it anyway. Some money coming in is better than none. The market will rebound eventually, and salaries will go up again. When that happens, you will be able to find a new role that will pay you appropriately. I left Microsoft for a second time when the market rebounded, and I got an offer for more than my old salary from somewhere else.

If the offer is much, much too low, take it. Keep looking for another role, but now with some security. No one says you have to put every position on your resume.

What you want to do and what you can do

Are you a developer, but a company is open to giving you a job as a tester or program manager? Are you an engineering manager, but a company is interested in talking to you about a product manager role?

If you are finding it hard to find a job doing what you want to do, it may be time for a temporary (or permanent) career change.

I wouldn’t automatically recommend this, though. If you switch into another role, when the market opens up, you may find it hard to go back to your preferred job. The market now sees you as a product manager or tester and may not consider you for a development role (especially if you are in the new position for a while). You may find that you enjoy the new job and want to pursue a new career, which could be a benefit. This situation happened to a few friends of mine during the 2008 crash.

If you decide to take the career-switching role out of necessity, make sure you keep your development chops up: contribute to open source, build apps or sites, whatever keeps your skills up-to-date.

You may be tempted to take a role outside the industry. This should always be the absolute last resort. Even with a strong resume, you may find it hard to get back in if you are in a very different field for a few years.

The sad fact for those who struggle during these periods is that most folks in the field will keep their jobs. When their companies start hiring again, these people will have a strong survivor’s bias. They may not understand the choices you had to make.

Build (and maintain) your network

Keeping up with your friends in the industry is probably going to be your best bet at finding a new role. Your friends can get you past the gatekeepers at the companies and make sure you are seen. They also may have more insight into what roles are open.

At first, it may be difficult to reach out to them. You may be embarrassed about the situation you are in. Get over it.

If you have been in the same company for a long time, or don’t have a big network in your area, start attending meetups or local conferences. Meet developers at other companies. You are likely to meet a lot of other folks in your situation, this is ok. You can form a group to share tips about companies hiring, maybe they may know someone at a company with a role appropriate for you.

Stay in your safe harbor

If you have a good job, with a good salary, keep it. Build your savings because even good companies don’t always survive. If you were considering that it might be time to move on and find a new role, don’t.

Even if you have an offer in hand, when companies hit a rough patch, after freezing hiring, they start rescinding offers. A friend of mine left his steady job during the bust to join another established company. He quit his old job and then the weekend before he started his new one, his offer was rescinded. He was now unemployed. His former company didn’t want him back. They got someone more senior for his role at the same salary.

The Reality

If you have been privileged to not know a time when you were worried about money, this will be scary. Hopefully, you find a new job, and this time will be brief. Many people in the world are not that lucky. They live constantly worrying about how they will pay their rent, or feed their families. When you are on the other side of this, realize how lucky you are and take your new perspective to be a better, more empathetic person. Do your best to help those in need, now that you have an understanding of what their reality is.

It will get better

Economies are cyclical. After the dot-com bust, there was exceptional growth in the tech industry. After the 2008 contraction, the tech sector went back into massive growth mode. If you lose your job and find it hard to get a new one, don’t despair. Things will get better. Until then, just focus on doing what you need to until that happens. Learn from this experience and be ready for the next contraction, because there will be one. Always.

If you don’t lose your job and you are in a position to make hiring decisions, try to be human. If you interview someone who seems to have lost all hope, try to see the person underneath who has had some bad luck. If you were lucky enough not to lose your job, don’t think you are better than those who did. Ask about their choices. Don’t assume that if someone went from being a developer to doing another job that it was a deliberate choice. Understand their story before making a decision.

These are amazingly challenging times for many people. Remember that if you lose your job during this downturn, even if things seem very bleak, you are probably still better off than 95% of the world’s population. If you want to grow your skills while looking for a job, you could build a website for a charity. That will leverage your skills, build your confidence, and do something for others too.

We’ll get through this.

A simple tip for prospective job seekers

If you are graduating with a degree in Computer Science and you are applying to companies in the software field; it is probably not a good idea to say something like “I’m looking for a job where I don’t have to sit in front of a computer all day” in your summary statement.