Jackson Owago's Blog

Do Startups Prefer Specialized Skills or a Strong Work Ethic and Willingness to Learn? You’ve seen the job ad before. “We need a self-starter with five years of experience in a fast-paced environment. Must know Python, manage their own projects, thrive under pressure, and be a team player.” It sounds like every other startup job post, right? But when you sit across from a candidate who may not tick all the boxes but lights up when talking about learning new things, what do you do? This is the hiring dilemma that almost every startup faces. Do we go for candidates with deep technical skills, or do we bet on someone eager, adaptable, and ready to grow? Skills vs. Mindset — What Are We Really Hiring For? Let’s be clear. Specialized skills matter. If you’re building software, launching a new product, or managing investor funds, you need people who know what they’re doing. But in startups, job descriptions are living documents. Roles evolve. Priorities shift. Today’s growth hacker may need ...

  Is Hiring New Talent Costing You More Than Keeping the Ones You Have? If you work in HR, you may have wondered if it is actually cheaper to retain a current employee rather than hire a new one. This blog simplifies the hiring process, making it clear, practical, and relevant. I will explore the various costs associated with hiring a new employee, including the time spent reviewing resumes, as well as the expenses of onboarding and training. Additionally, I will address less obvious costs, such as lost productivity and the time managers spend conducting interviews. Then I will compare that to what it takes to keep your best people happy and growing in their roles. Retaining is usually the smarter move, both for your budget and your company culture. This post is for HR leaders who want to be more strategic with their time, energy, and hiring budgets. It's packed with insights you can use in your next boardroom pitch or talent planning session. I will be looking to answer the follow...

Hiring on a Budget? Here’s What Actually Works “We can’t compete with the big guys on salary. How are we supposed to hire anyone great?” A founder said this to me last week, and I nodded. It’s something I’ve heard from startups, nonprofits, and even mid-sized companies. And it’s a real concern. The Problem Let’s face it, money talks. But not every company has the budget to pay top-tier salaries, especially in today’s competitive talent market. That doesn’t mean you’re out of the game. It simply means you need to think a little creatively. What You Can Do Instead Here are a few things that don’t cost a fortune but do catch candidates’ attention: Showcase Purpose Today’s candidates want to work somewhere meaningful. If your company is solving a real problem or making life better in some way, talk about it. Ensure your purpose is clearly communicated on your website, in your job ads, and during interviews. Be Flexible (Really Flexible) Flexibility is the new currency. Can people work remo...

Why You Should Chart Your Path to Chief Commercial Officer Let’s be honest. You didn’t get into sales, marketing, or business development just to hit quotas and call it a day. You’re here because you want to drive real impact. You want a seat at the table where strategy meets execution, where revenue meets vision. That’s the CCO role. But here’s the problem.  Too many talented professionals get stuck in the middle. They jump from one role to another, waiting for someone to hand them the keys to the C-suite, only to realize too late that no one is coming to promote them into leadership. It’s not about luck. It’s about design. If you’re serious about becoming a Chief Commercial Officer , you need a real plan—not just hard work, but the right work. This isn’t just another career guide. It’s your roadmap to the top. What Does a CCO Career Map Look Like? Career mapping isn’t about waiting for opportunities—it’s about creating them. It’s the difference between: Drifting from role to role...

How Women Leaders Can Set Boundaries Without Guilt Saying no doesn’t make you selfish—it makes you a better leader. Discover how to set boundaries that empower you and your team. Did you know that 71% of women feel guilty when they say no at work, even when they’re overwhelmed?  From societal expectations to workplace pressures, women are often conditioned to be accommodating, putting others’ needs before their own.  But here’s the truth: setting boundaries isn’t selfish—it’s essential for effective leadership. The fear of being seen as difficult or unapproachable can hold women back from enforcing boundaries, leading to burnout, resentment, and reduced productivity.  This post is your guide to setting boundaries confidently, without guilt, and becoming the leader you’re meant to be. Why Women Struggle with Setting Boundaries Women face unique challenges when it comes to setting boundaries: Societal Conditioning: From a young age, women are often taught to prioritize ot...

How Women Can Build Supportive Networks That Propel Them Forward Your network is your greatest asset. Today, we’ll explore the journey from being a mentee to becoming a mentor—and why embracing both roles is key to effective leadership. Did you know that 85% of jobs are filled through networking, yet women are 25% less likely than men to have access to senior leaders who can advocate for their career growth? Networking and mentorship aren’t just nice-to-haves—they’re critical tools for breaking barriers and achieving leadership success. But for many women, building a strong professional network can feel daunting. Whether it’s imposter syndrome, lack of access, or uncertainty about where to start, the challenges are real.  This post is your roadmap to creating meaningful, supportive connections that will propel you forward and help others do the same. Why Networking & Mentorship Matter for Women Networking and mentorship are more than just buzzwords—they’re game-changers for car...

Women Can Lead Authentically Without Apologizing Did you know that 76% of women feel pressured to downplay their accomplishments to avoid being seen as “too assertive”? This phenomenon, often called the likeability trap, creates a psychological conflict for women in leadership: be respected or be liked, but rarely both. From softening their tone to over-apologizing, many women feel compelled to conform to outdated expectations of how a leader “should” act. But here’s the truth: authentic leadership isn’t about pleasing everyone—it’s about leading with confidence, clarity, and conviction. Here’s how to escape the likability trap, embrace your authentic self, and lead unapologetically.  Let’s dive in. Understanding the Likeability Trap The likeability trap is the double standard women face when they lead assertively. While decisive men are praised as strong leaders, decisive women are often labeled as “bossy” or “difficult.” Societal Expectations: Women are often socialized to be nu...