Building successful learning and development programs: Insights from our expert webinar

We recently hosted a webinar on "How to Build a Successful Learning & Development Program" featuring author, coach, and learning & development expert Sarah Cannistra who oversees training for Rippling’s 3,500+ employees. The session was packed with practical insights on creating effective training programs that drive real results.

For those who couldn't attend or want to revisit the key takeaways, we've compiled Sarah's insights and answered the most common questions from our audience below.

4 key tips from a learning & development expert

#1) Building effective L&D programs as a team of one

Sarah knows firsthand the challenges of building and scaling an effective L&D program with limited resources. In previous roles, she found herself trapped in a cycle of administrative tasks rather than focusing on strategic initiatives.

"In my last role starting off as a team of one with basically zero budget, I ended up spending the majority of my time on manual tasks rather than being strategic," Sarah shared. "About 90% of my time was spent sourcing and vetting content, and the rest on administrative matters to make sure the right people were in the right training at the right time."

With limited resourcing and only so many hours in the day, it’s essential to think through a sustainable structure for your program from day one. For Sarah, that has meant leveraging Rippling's LMS to automate critical administrative tasks. No more manually assigning courses or tracking progress—Rippling automatically enrolls employees in the right courses based on their roles, tenure, or other attributes in the system and sends reminders for course completions. For instance, when an employee is promoted to a manager position, the system automatically enrolls them in a "Welcome to Management" course.

Sarah also emphasized the importance of finding allies within the organization—rallying colleagues who are interested in helping co-facilitate, getting leaders involved in leading sessions, and creating pathways for others to be co-creators. Identifying these early adopters can give you powerful champions for expanding program resourcing down the road, and they provide a valuable source of input for the never-ending process of fine-tuning your learning initiatives.  

#2) Sourcing high-quality, engaging content for your teams

During the webinar, many attendees identified finding quality training content as one of their biggest challenges. Sarah has experienced this as well, sharing that in her previous position, she spent countless hours scouring the internet and YouTube with no reliable way to determine what content was reputable or aligned with business needs. 

Through Rippling's partnership with Go1, Sarah can now find high-quality content in a matter of minutes thanks to an extensive library of over 80,000 courses from leading content providers. Go1 offers training across a wide range of topics including business skills, public speaking, and data analysis—all available in over 40 languages to support global teams.

Having access to this extensive content library has been a game-changer, but Sarah knows that great content alone isn't enough. She emphasized that the key to making these courses truly effective is personalization. By using Rippling's built-in workflows, she’s able to deliver courses at the right moment in the employee lifecycle. "We can automatically trigger specific training when an employee changes roles or completes their first 90 days," she noted. 

Sarah explained that external content is just one piece of her training strategy—she also creates materials unique to Rippling. For company-specific knowledge, she uses Rippling's Course Builder to create custom content incorporating videos, quizzes, and interactive elements that engage employees. This tool helps her develop training that reflects Rippling's unique processes, culture, and best practices. 

#3) Measuring the success of your L&D initiatives

Many attendees raised another critical challenge during our discussion: proving ROI and program impact for L&D initiatives. Sarah addressed this directly, sharing practical approaches to demonstrating value that can help overcome this common hurdle.

She recommends focusing on three key areas to prove the effectiveness of L&D programs: 

1. Employee engagement scores: It is key to track whether employees feel they have the resources to support their development and what other opportunities they'd like to see. Rippling’s built-in Surveys tool makes it easy to gather this feedback regularly.
2. Qualitative reflection surveys: Understanding what employees will do differently after completing a course or program provides valuable data about their takeaways. Sarah uses Rippling to automatically send surveys upon course completion, ensuring consistent feedback collection without additional administrative work. 
3. Business outcomes: The success of L&D initiatives should ultimately tie to business outcomes. For example, if a program is designed to improve customer interactions, it should correlate with metrics like customer satisfaction scores or sales performance. 

"I like to 'start with the end in mind' when it comes to metrics," Sarah advised. "Ask stakeholders: What will success look like to you? What behaviors will change? What key indicators will tell you this training worked? This ensures you backward engineer into those metrics, and when you do influence those metrics, that stakeholder will continue to champion your programs."

#4) Driving engagement through effective marketing

Many attendees noted that despite creating valuable training programs, they struggle with low participation rates because employees are busy and overwhelmed with competing priorities. During our discussion, Sarah emphasized that even the best content won't deliver results if employees don't engage with it. "If you aren't creating hype for your programs, who will?" she asked.

She shared several strategies that have worked well for her:

• Creating a "wrapped" like Spotify, highlighting programs, testimonials, and their impact on both the business and individual employees
• Developing "trailers" for new programs to generate buzz
• Building a network of amplifiers—leaders on other teams, HR partners who work closely with managers—to promote programs throughout the organization

Top questions from our audience

During the webinar, our audience asked insightful questions about building successful L&D programs. Here are the top questions and answers:

Q: For organizations just starting with an L&D program, what advice would you give to ensure they're setting themselves up for success?

When starting an L&D program, focus on two key strategies.

First, prioritize low-hanging fruit by focusing on high-value initiatives that can be implemented quickly. Getting high-quality content that addresses immediate learning needs is more important than trying to solve all learning problems simultaneously. Having access to pre-built, high-quality content can also be a game-changer when starting out. Sarah noted that Go1's extensive library allows her to quickly launch essential training programs without having to create everything from scratch.

Second, adopt an iterative approach by piloting programs with small groups and refining based on their feedback. Successful L&D programs are never truly "done"—Sarah noted that even established programs like Rippling's manager onboarding continue to evolve based on new feedback.

Q: How can a team of one manage competing priorities in L&D?

Managing competing priorities as a team of one requires strategic prioritization. Start with initiatives that deliver maximum impact with minimal effort and leverage technology to automate routine tasks.

Rippling's tools help teams of one manage competing priorities and free up time for strategic work. Automated enrollment rules assign courses based on employee attributes, while built-in reminder systems ensure timely completion without constant follow-up. And by enabling employee self-enrollment, Rippling not only reduces administrative burden but also empowers employees to take ownership of their development journey. 

Q: How do you convince leadership to take on L&D initiatives?

Sarah highlighted three major challenges and how she overcame them. 

First, Sarah explained that securing leadership buy-in requires using data to show the impact and value of learning programs. Rather than focusing on completion rates or course enrollments, she recommends approaching conversations from the perspective of business impact.

Second, make sure to align your L&D strategy with existing company priorities and challenges. When proposing a new initiative, she first meets with key stakeholders to understand their business goals, pain points, and what success metrics matter most to them. This approach ensures that training programs directly address real organizational needs rather than existing in isolation.

Third, don’t forget about the power of quick wins. She recommends starting with smaller, targeted initiatives that can show measurable results within 90 days. These early successes create momentum and build credibility for more ambitious programs down the road, transforming leadership from skeptics into champions for learning and development.

Q: How do you balance what the company needs versus what employees want for their own growth?

For essential skills, Sarah partners with stakeholders to identify critical gaps—understanding what behaviors and skills define success in each role. Rather than creating everything from scratch, she looks for opportunities to amplify what's already working in the organization.

To keep employees feeling supported in their development, which is key for retention, Sarah recommends pairing a focus on essential skills with an approach that consistently solicits employee input. At the end of every training, she shares a survey asking employees how they plan to implement what they learned and what else they would want to develop in.

Take your L&D programs to the next level 

Looking to transform your learning and development initiatives? Watch the full webinar recording. And if you'd like a personalized consultation on how Rippling can support your L&D goals, book a meeting with one of our talent experts today.

This blog is based on information available to Rippling as of March 13, 2025.

Disclaimer: Rippling and its affiliates do not provide tax, accounting, or legal advice. This material has been prepared for informational purposes only, and is not intended to provide or be relied on for tax, accounting, or legal advice. You should consult your own tax, accounting, and legal advisors before engaging in any related activities or transactions.