How to upskill your startup team for scaling

Startups that reach the late stage have already solved the hardest problem: survival. Customers are paying, the product works, and momentum is building.

But scaling is a different game. The skills that got the company here aren’t always the ones needed to get it further. Founders often think about hiring new talent to bridge the gap. That works, but it’s expensive, risky, and slow.

The better option is to upskill the team that already understands the product, culture, and customers. When done right, this keeps the company’s core DNA intact while unlocking the next level of growth.

Some of the best scale-stage startups succeed not because they hire better, but because they make their existing team better. Here’s how to do it.

1. Assess skills gaps

When people think of scaling, they often stress about operations and revenue. But an overlooked part of scaling is making sure your team has the right skills to handle new challenges.

A common mistake founders make is assuming their early team can simply “figure it out” as the company scales. But what worked at 20 employees may break down at 100. Processes get more complex, decision-making slows, and gaps in leadership or expertise start to show.

That’s why the first step in upskilling your team is to identify the gaps between where you are now and where you need to be.

The best way to do this is through a skills audit – a structured way to assess what your team is good at today and what skills will be critical for future growth.

How to conduct a skills audit

A skills audit is useful to help your team for the next stage of growth. There are several ways to gather insights:

• Performance reviews: Regular reviews give you a sense of who’s excelling and who needs support. If done well, they reveal patterns, for example, like someone who’s great at solving problems but struggles with communication.
• 360-degree feedback: Ask managers, peers, and direct reports for feedback. This helps uncover blind spots – things someone might not realise about themselves but that others see clearly.
• Self-assessments: Get employees to rate their own skills. This helps them reflect on their strengths and weaknesses and gives you a sense of where they think they need help.
• Surveys & skill inventories: A structured survey can show you the full picture of your team’s abilities. It’s like mapping out all the skills in your company so you can spot gaps before they become problems.

Once you’ve mapped out your team’s skills, you need to compare them against what your company will need to scale.

Why you need to align skills with business goals

Not every missing skill is a problem. You should only focus on gaps that directly impact the outcomes you’re aiming for. If a skill isn’t essential to a role, it’s not a priority for upskilling.

This helps you avoid wasting time on training that won’t move the needle. To do this, some of the considerations include:

• What skills are missing that could slow down our growth?
• Which roles will be most critical in the next 12-24 months?
• Who on the team has the potential to grow into these roles with the right training?

If leadership gaps are a problem, investing in management training makes sense. If marketing performance is weak, upskilling in performance marketing or analytics might be the answer.

When you identify and fix skills gaps early, you set your team up for growth, without the stress and cost of last-minute hiring.

2. Set clear learning objectives

Once you’ve identified the gaps, the next step is making a plan to close them.

Upskilling isn’t just learning new things, it’s learning the right things in a way that helps both the company and the employee. That’s why clear learning objectives matter. Without them, training can feel scattered and ineffective.

Employees need to know what they’re learning, why it matters, and how it will help them grow. When they see the value, they’re more engaged, and the business gets real results. Setting great goals will help you with that.

Use SMART goals to focus learning

A vague objective like “improve leadership skills” doesn’t provide a roadmap for success.

It’s also a cliche at this point but you really should use SMART goals to make learning structured and measurable. SMART stands for:

• Specific: Clearly define what needs to be learned.
• Measurable: Track progress with defined outcomes.
• Achievable: Ensure the goal is realistic given the person’s role and experience.
• Relevant: Align learning with business needs and personal career growth.
• Time-bound: Set a deadline to create urgency and focus.

For example, instead of saying, “Improve financial skills,” a SMART goal would be:

“Complete an advanced financial modelling course and apply it to our next quarterly budget planning by the end of Q2.”

Or instead of “Become a better people manager,” it could be:

“Attend a leadership training program, implement weekly one-on-ones with direct reports, and improve team engagement scores by 15% within six months.”

We find that even when people know to do this, most startup goals lack timeframes and measurement. So, don’t overlook these, even if it feels easier in the short time.

Make learning personal and valuable

People are far more likely to engage in upskilling if they see how it benefits them, not just the company. Founders and managers should communicate:

• How learning a new skill will make their job easier or more rewarding.
• How it aligns with their personal career goals.
• What opportunities could open up for them as a result.

For example, an account manager learning enterprise sales skills could move into a high-value sales role. A software engineer improving data analytics skills could transition into a product leadership position.

The best strategy is to connect training with career progression. When employees see a future in the company, they’re far more invested in their own growth. And when learning is structured with clear objectives, the business benefits just as much as the person learning.

3. Choose the right learning methods

Now you’ve identified the skills gaps and set clear learning objectives, the next step is deciding how employees will learn. Not all training methods work the same way for every skill or every person. The best approach combines structured learning with hands-on experience, so employees can immediately apply what they learn.

A mix of formal training, mentorship, and real-world application is the fastest way to upskill a team. Here’s how to choose the right methods for different needs.

1. Workshops and training programs

Workshops provide focused, high-impact learning in a short period. They can be internal (run by company leaders) or external (taught by industry experts). These sessions work best for:

• Leadership development
• Technical skills (e.g., financial modelling, coding, sales techniques)
• Communication and soft skills (e.g., negotiation, public speaking)

For example, if the company is struggling with product-led growth, a structured workshop on growth hacking strategies could equip the marketing and product teams with practical techniques they can test immediately.

2. Mentoring and coaching

Some of the best learning happens through one-on-one guidance from experienced professionals.

• Peer mentoring allows employees to learn from colleagues who have mastered specific skills.
• Leadership coaching helps emerging managers develop their ability to lead teams effectively.
• Reverse mentoring allows junior employees to teach senior leaders about new trends (e.g., AI tools, social media strategies).

For example, if a software engineer is transitioning into a product management role, pairing them with an experienced product leader can speed up their learning curve.

3. Online courses and certifications

Platforms like LinkedIn Learning, Coursera, Udemy, and internal Learning Management Systems make self-paced learning accessible. These work well for:

• Technical skills (e.g.,data analytics, programming, digital marketing)
• Industry certifications (e.g. project management, cybersecurity, compliance)
• Soft skills (e.g. emotional intelligence, leadership)

Online courses are great for foundational learning, but they work best when combined with practical application. Otherwise, employees might complete them but never apply the knowledge.

4. On-the-job training

Real learning happens when employees take on new responsibilities that challenge them. On-the-job training includes:

• Job rotations – Employees work in different roles or departments to broaden their skillset.
• Cross-functional projects – Teams from different departments collaborate on a strategic initiative.
• Shadowing – Employees observe experienced team members to learn by watching.

For example, if a customer success manager is interested in sales, they could start shadowing sales calls before transitioning into a hybrid sales role.

5. Industry conferences and networking

Attending conferences, summits, and networking events allows employees to:

• Stay updated on industry trends and best practices.
• Meet experienced professionals who can offer insights and mentorship.
• Get inspired by successful leaders and case studies.

For example, sending a marketing team member to a growth marketing conference could help them bring back new strategies to apply in the company.

Make sure you do your research on these before taking them on as an upskilling strategy. There’s plenty of conferences that bring everybody together, but don’t give much back in terms of education.

The best approach is a blended learning strategy

A strong upskilling program doesn’t rely on just one method. It uses different methods to help employees learn, remember, and apply new skills in real situations.

For example:

• A sales team could take a workshop on negotiation, practice in role-play sessions with a mentor, and then test their skills in real client meetings.
• An engineering lead could complete an online leadership course, get paired with a mentor, and gradually take on more management responsibilities.

When you can apply multiple learning methods, you help your employees turn new knowledge into real skills that drive business growth.

4. Create a culture of continuous learning

Upskilling isn’t a one-time event. For a startup to scale successfully, learning needs to be part of everyday work, not an occasional workshop or training program.

The best late-stage startups create a culture where learning is expected, supported, and rewarded. When employees are continuously improving, the company stays adaptable, innovative, and ready for whatever challenges come next.

1. Encourage knowledge sharing

Knowledge shouldn’t stay locked inside individual team members – it should spread across the company. The more a team shares what it knows, the faster everyone levels up. Some ways to do this:

• Lunch-and-learns – Employees present what they’ve learned from a recent project, course, or conference.
• Internal wikis or knowledge hubs – A central place where best practices, strategies and lessons learned are documented.
• Shadowing & peer mentoring – Team members observe each other’s work to gain insights from different roles.

For example, if a marketing manager learns a new SEO strategy, they should share it with the team so everyone benefits.

If an engineer finds a way to optimise a system, that knowledge should be documented and shared with the rest of the tech team.

2. Recognise and reward learning

People are more likely to prioritise learning if they see it being valued by leadership. Recognition can be:

• Public praise – Highlight employees who’ve upskilled in company meetings or newsletters.
• Promotions and career growth – Give leadership opportunities to those who develop key skills.
• Learning incentives – Offer bonuses, stipends, or perks for employees who complete critical training.

Let’s say you have a customer support team member who takes the initiative to learn sales skills and successfully closes a few deals. Recognising their effort and providing a clear career path to a sales role can keep them motivated.

3. Allocate time for learning

People won’t upskill if they’re too busy with daily tasks. Companies need to make space for learning within work hours.

• Dedicated learning time – Set aside at least one hour per week for employees to focus on professional development.
• Microlearning – Encourage small, frequent learning activities instead of long, one-off training sessions.
• Learning sprints – Focused, short-term upskilling projects tied to real business needs.

For example, a product team could dedicate Fridays from 3-4 PM to learning sessions where they explore new industry trends or tools. If you show that you care about learning enough to allocate time to it, your team is more likely to value it.

4. Help them apply learning immediately

People learn best when they can apply new skills right away. If employees complete a course or attend a workshop, they should immediately use that knowledge in their work.

• Stretch projects – Assign tasks that push employees just beyond their current skill level.
• Hands-on application – Give team members opportunities to implement what they’ve learned in real scenarios.
• Real-time feedback – Encourage managers to provide quick feedback on new skills being developed.

To give an example, if an operations manager takes a course on process automation, they should be given a project to optimise an internal workflow as soon as possible. This keeps the content fresh and active in their mind.

5. Develop a growth mindset

A culture of continuous learning starts at the top. Founders and leaders need to model curiosity and self-improvement.

If employees see leadership investing in their own learning – attending conferences, seeking mentorship, experimenting with new strategies – they’ll follow suit.

When startups make learning part of daily work, growth becomes second nature. Employees stay engaged, the team evolves, and the company scales with a workforce that’s always improving.

5. Provide support and resources for learning

Upskilling only works when employees have the right support. If learning is too expensive, difficult to access, or feels like extra unpaid work, people won’t do it.

Startups that take upskilling seriously encourage learning, but they also actively remove barriers by offering the resources employees need to grow.

Here’s how to give your team the support they need to succeed.

1. Offer financial support for learning

Investing in your team’s development is an investment in your company’s future. If employees see that the company is willing to cover the cost of learning, they’re far more likely to take it seriously.

Some ways to provide financial support:

• Course fee reimbursement – Cover part or all of the cost for relevant courses, degrees, or certifications.
• Training stipends – Provide an annual budget employees can use for workshops, books, or courses.
• Conference sponsorship – Pay for employees to attend industry events that align with company goals.

For example, if a marketing team member wants to get certified in Google Ads, the company could reimburse the cost of the course and exam, knowing that their improved skills will benefit the business.

2. Give them mentors or career coaches

Formal education is useful, but mentorship is often the fastest way to grow. Having an experienced guide makes learning more engaging and practical.

Some ways to provide mentorship:

• Internal mentoring programs – Pair employees with senior team members who can help them develop key skills.
• External career coaching – Bring in industry experts or executive coaches to help leaders level up.
• Cross-team learning – Encourage employees to shadow or collaborate with other departments to gain broader experience.

To illustrate, if an engineer is transitioning into a technical leadership role, pairing them with a seasoned CTO for monthly coaching sessions can help them develop the mindset and skills they need.

3. Make it easy to access to learning materials

Employees should never struggle to find learning resources. Make sure training materials, best practices, and knowledge-sharing platforms are easy to access.

Ways to improve access:

• Internal knowledge hubs – Create a centralised place (e.g. Notion, Confluence, Google Drive) where employees can find training guides, recorded workshops, and best practices.
• Company-funded learning platforms – Provide free access to online courses or training programs
• Recommended reading lists – Curate books, podcasts, and articles relevant to different roles and career paths.

So let’s say your company wants to improve data-driven decision-making.

To do this, you could provide a shared library of analytics resources and encourage employees to complete a short data literacy course. This would make it easier for them to learn and, therefore, more likely to do it.

When startups make it easy for employees to learn, people don’t just improve their skills – they become more engaged, motivated, and committed to the company’s success. A business that invests in its people builds a team that’s ready to scale alongside it.

6. Track progress and measure learning impact

Upskilling is only valuable if it leads to real improvement. Many companies invest in training but fail to track whether it’s actually making a difference.

So that your upskilling efforts are effective, you need to monitor engagement, measure results, and adjust your approach based on what works.

Here’s how to track progress and ensure learning leads to tangible business outcomes.

1. Monitor employee engagement

The first sign of whether an upskilling program is working is engagement. If employees aren’t actively participating, something needs to change.

Ways to track engagement:

• Course completion rates – How many employees finish online training or workshops?
• Participation in knowledge-sharing sessions – Are employees attending lunch-and-learns or internal training sessions?
• Feedback surveys – Do employees feel the training is useful and relevant to their work?

You might feel confident in your upskilling by offering a leadership course to employees. But if you find they consistently drop out of their training midway, it could indicate the content isn’t engaging, the sessions are too long, or they don’t see the immediate value.

2. Measure improvement

Beyond participation, the real test is whether employees are actually improving. Set clear performance indicators that align with learning goals.

Some examples of upskilling KPIs include:

• Sales training: Increase in conversion rates or deal size.
• Leadership development: Higher employee engagement scores or improved team performance.
• Technical training: Faster project completion times or reduced errors.
• Customer success training: Lower churn rates or better customer satisfaction scores.

You’ll find that most skills are measurable with a little work.

For example, if the goal was to improve data literacy in the marketing team, one KPI could be the percentage of marketing decisions now backed by data insights – versus gut instinct.

This could be measured by documenting the insight that informed the decision as part of the marketing campaign plan.

3. Use quarterly growth plans and stretch projects

One of the best ways to track upskilling success is through real-world application.

• Quarterly Growth Plans: Each employee sets learning goals for the next three months, tied to their role and company objectives.
• Stretch Projects: Employees are assigned tasks slightly beyond their current skill level, forcing them to apply what they’ve learned.

If a customer success manager has been training in enterprise sales, a stretch project could involve leading a pitch for a high-value client. Their ability to handle objections, navigate multi-stakeholder deals, and close the sale would be a strong indicator of their growth.

It’s best to pair this with mentorship and support, in order to not overwhelm your employees, and to give them the best chance for success.

4. Adjust based on feedback and results

A good learning program isn’t static, it should evolve based on what’s working and what isn’t. If employees aren’t improving, it’s a sign that something in the process needs to change.

So take a step back and ask some key questions:

• Is the training too theoretical and not practical enough?
• Are employees too busy to focus on learning?
• Do they need more mentorship or hands-on experience?
• Is the skill relevant to our scaling needs?

Through this data, you can refine your approach to upskilling. This gives your team the best shot at building skills in a way that helps both them and the business.

7. Align upskilling with career progression

People are more motivated to upskill when they see a clear connection between learning and career advancement.

If employees believe that developing new skills will help them move into leadership roles, take on bigger responsibilities, or increase their earning potential, they’ll be far more engaged in the process.

For startups, aligning upskilling with career progression isn’t just for keeping employees motivated, it’s also a powerful retention tool. When people see a future in the company, they’re less likely to leave, reducing turnover and the need for constant hiring.

1. Offer clear pathways for promotion and new roles

Upskilling should be tied to real career growth. Employees need to know what’s possible for them if they invest in learning.

Here are some ways to create clear career paths:

• Defined role progressions – Outline what skills and experience are required to move from one level to the next.
• Internal job opportunities – Prioritise promoting from within before hiring externally.
• Skills-based promotions – Reward employees who develop key skills with new responsibilities and higher roles.

For example, instead of simply requiring “five years of experience” for a leadership role, create a structured path like:

• Marketing Manager → Head of Growth
• To move up, employees need to develop skills in campaign strategy, team leadership, and performance analytics.

In making the requirements more transparent, employees know what to aim for and can take control of their own growth.

2. Use upskilling as a retention and motivation tool

Employees who feel stagnant are more likely to leave. Offering structured learning opportunities and clear career growth makes employees feel valued and invested in the company’s success.

Ways to use upskilling for retention:

• Regular career development check-ins – Managers discuss learning goals and career aspirations with employees.
• Special projects and leadership opportunities – Give high-potential employees real experience in leadership before promoting them.
• Personalised learning plans – Each employee has a tailored growth roadmap tied to their interests and company needs.

For example, if an engineer wants to transition into a product management role, the company can provide mentorship, relevant courses, and opportunities to work on product strategy.

This not only helps the employee grow but also fills an internal skill gap without hiring externally.

3. Make career growth part of company culture

Upskilling should be the norm, not the exception. When learning is baked into the company’s culture, employees feel constantly challenged and engaged.

• Encourage continuous development – Make it clear that career growth isn’t just for “high performers”—it’s for everyone.
• Celebrate promotions and internal mobility – Recognise employees who grow within the company.
• Ensure leadership development starts early – Don’t wait until someone is already in a leadership role to train them.

When you align learning with career progression, you don’t just create stronger employees, you build a more resilient, high-performing team that stays with you for the long haul.

Final thoughts

If you want your startup to scale, focus on building from within.

The team that got you here already understands your product, your customers, and your culture. Investing in their growth is the fastest, most effective way to reach the next stage.

Upskilling strengthens your team, keeps momentum high, and creates a culture of continuous learning. When people grow, the company thrives. The best late-stage startups succeed by empowering their teams with new skills, fresh ideas, and greater confidence.

Scaling can be more than simply expanding the business. It can also mean unlocking the full potential of the people driving it forward. And that can be a cheat code for success.