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SMB wins and lessons of 2023 – and what’s planned for 2024

2023 was a crazy year. We asked the SMB community for their takeaways and lessons, and summed up their key wins and lessons and what they're planning for 2024. Dive in!

Keith MacKenzie
Keith MacKenzie

Passionate about human resources, employment, and business management, and an expert at sharing that expertise.

Every year, we like to query hiring teams and SMB employers the world over to understand:

  • What their biggest challenge of the past year was
  • What their biggest triumph of the past year was
  • What they would plan for differently if they knew then what they know now

And also:

  • What they anticipate will be their biggest challenge for the upcoming year
  • What they anticipate will be their biggest triumph for the upcoming year
  • What they’re planning for the upcoming year after what they’ve learned from the past year

When you ask such a wide range of questions, you’ll get a fascinating array of answers. We did this in December 2021, and again in December 2022.

This time, in December 2023, we got more than 120 responses to our query, and we’ve packaged their responses into 11 major themes.

Read on and learn what the top wins and lessons of 2023 were for employers, and what they’re planning for 2024:

1. Adopting remote work models

Many respondents discussed the shift to remote work arrangements, focusing on the challenges and opportunities this change presents.

Ben Richardson, Founder & Director, Acuity Training:

“I have further optimized remote work setups within my team by leveraging technologies to facilitate seamless communication, collaboration, and productivity among remote teams.”

Eugene Klimaszewski, President, Mammoth Security:

“One of the key advantages we’ve experienced at our company is the flexibility it offers. As remote entrepreneurs, we can operate from virtually anywhere, tapping into a diverse talent pool without the constraints of physical office spaces.”

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Warner Quiroga, President/CEO, Prestige Homebuyers:

“Embracing remote work has taught us that we can achieve impressive results while offering our employees a flexible, fulfilling work environment. We can keep pushing the boundaries and setting new standards for remote work within the real estate industry.”

Nathan Jacobs, Senior Researcher, The Money Mongers Inc.:

“Our biggest win was rolling out a flexible work model. We struck a balance between remote and office work, leading to a spike in productivity and happier employees.”

Jason Smit, CEO, Contentellect:

“Basically, 2023 proved the prescience of remote work, and as old models are still playing catch up, I think our position solidifies as the exemplar.”

Marc Massad, Business and Marketing Director, VelocityPaddle:

“Our most notable accomplishment in 2023 was establishing a flexible work structure, more especially a hybrid model that allowed for both in-office and remote work. We made this strategic step because we care deeply about our employees and want to create a workplace that supports their different requirements. Not only did the hybrid model provide more leeway, but it also greatly improved both contentment in one’s work and productivity.”

James Gibson, Digital Marketing Manager, Camsurf:

“I would stress the significance of strong channels of communication and deliberate attempts to foster team cohesiveness if I could go back in time to December 2022. The shift to the hybrid work model may have gone more smoothly if early investments in digital collaboration tools and team-building exercises had been put in place.”

Kelly Indah, Editor in Chief, Increditools:

“To be successful and bring up new ideas, tech leaders need to be able to see problems coming and figure out how to fix them. In 2024 it’s hard to work with people who are far away. A tough issue needs direction and teamwork when many people work from home.”

2. Fine-tuning the hybrid model

The hybrid model itself posed challenges and lessons – namely, establishing remote and in-office collaboration to maintain productivity and team spirit.

Sebastian Petrosi, CMO,

“[Challenge for 2024]: Balancing the hybrid work model effectively. As we continue with remote and office-based work, ensuring equal opportunities and a cohesive company culture will be a challenge.”

Lisa Geller, Senior Content Writer Specialist, Eventify:

“Our key challenge in 2023 centered around maintaining seamless communication and cohesion in a hybrid work environment. Balancing remote and in-office collaboration required strategic adjustments. This challenge led us to invest in robust communication tools and innovative team-building activities to bridge the physical and virtual divide.”

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Dan Eastman, CEO & Founder, Ship Tracking:

“In 2023, I learned the significance of flexible work arrangements and prioritizing employee well-being. Remote work proved feasible, but maintaining team cohesion required deliberate effort. As we head into 2024, I’m focusing on refining hybrid work models, nurturing a supportive company culture, and using technology for seamless collaboration. Recognizing the importance of continuous learning, I’m investing in employee development programs to adapt to evolving industry demands and ensure a resilient and engaged workforce.”

Max Williams, Founder & CEO,

*Our most significant achievement in 2023 was successfully implementing a flexible work arrangement that catered to the diverse needs of our team. We adopted a hybrid model, allowing employees to balance remote work and in-office collaboration. This not only boosted overall job satisfaction but also improved productivity and work-life balance.*

Wendy Wang, Owner, F&J Outdoor:

“Our most significant accomplishment in 2023 was transitioning to a hybrid work model. We found that this flexibility boosted our employees’ morale and productivity. Our physical warehouse operations were balanced with remote administrative tasks. Our biggest challenge was maintaining consistent communication and team cohesiveness in this hybrid model. It was essential to ensure that no one felt left out or misinformed, whether they were in the office or working from home. If I could meet with my December 2022 self, I would encourage a more proactive strategy in adopting digital tools for better communication. It’s not just about using these tools but understanding how they can bridge the gap between our in-office and remote team members. Our aim for 2024 is to perfect our hybrid working model, by fine-tuning our approach towards employee engagement and maintaining a strong culture in this modern workspace. We anticipate our biggest challenge in 2024 to be the process of hiring and onboarding new employees in a hybrid environment. Making them feel part of our culture and ensuring they’re up to speed with their responsibilities will be crucial.”

3. Balancing work and life priorities

The challenge of maintaining a healthy work-life balance and preventing burnout in remote work environments is a common concern.

Shawn Plummer, CEO, The Annuity Expert:

“In 2023 our most significant accomplishment in workforce management was implementing a flexible work schedule that accommodated employees’ personal needs. This led to improved work-life balance and increased job satisfaction.”

Will Hatton, Founder & CEO, The Broke Backpacker:

“Heading into 2024, I would like my biggest accomplishment to be improving the work-life balance of all my employees. My team deserves a favorable and flexible working schedule, giving them time to handle their personal affairs. I also like to establish a mental health program that focuses on reducing work stress for my staff.”

Daniyal Sanaullah, Owner & CEO, SocialSharings:

“Our main focus at SocialSharings for the year 2024 is to establish a comprehensive employee well-being program. This program aims to prioritize mental health, work-life balance, and professional growth. By providing a supportive environment, we believe that our team will not only perform at their best but also experience a sense of fulfillment and job satisfaction. This holistic approach to workforce management aligns with our values and contributes to the long-term success of both individuals and the agency.”

Kelly Indah, Editor in Chief, Increditools:

“Being unable to separate work and personal life while working from home can cause burnout. They should get regular wellbeing checks, know how much work they have, and find a good work-life balance for their health. Stress-free work and happy employees go hand in hand.”

Mathias Ahlgren, CEO & Founder, Website Rating:

“We started 2023 in a strong position in terms of results, but morale was low. The team had been working so hard, and the work/life balance had started to slide. I knew it was only a matter of time before our work was affected, and anyway, I care about my staff. So, we decided to improve the employee experience in 2023, and I’m proud to say we have done just that. Because of this, we have hit all our targets.”

4. Cohering as a team

Maintaining team cohesion and a unified company culture is another recurrent theme, with many seeking innovative communication and team-building strategies.

Vipin Nayar, Founder,

“One insight we’ve gained is the importance of fostering a strong sense of community, even in a remote setting. Regular virtual team-building activities have been instrumental in maintaining camaraderie.”

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Michael Alexis, CEO,

“Employees who were worried about being overworked as their teams grew smaller soon came to see that with the right systems put into place, they could achieve just as much with a leaner team. Our biggest managerial accomplishment was being able to get employees onboard with these changes. We were able to achieve this in part by our history of repurposing employees in new roles and creating development and leadership opportunities. We also shared performance and victories to prove that these changes were bringing about results — for instance, we announced at our company retreat that our sales team achieved one of their biggest revenue months ever, despite being significantly smaller (about half) than it was at its peak.”

Michael Guinan, Founder, Subscription Stopper:

“We’re focusing on enhancing digital collaboration tools and strategies for effective remote management. Emphasizing mental health, work-life balance, and equipping leaders with tools to manage remote teams effectively are top priorities.”

5. Engaging employees

Strategies to deepen employee engagement and personal development are frequently mentioned, including tailored growth opportunities and mentorship programs.

Teresha Aird, Co-founder & CMO,

“Our biggest challenge was navigating the (quite dramatically) evolving landscape of employee expectations. Especially regarding work-life balance and career development opportunities. I expect the shift has largely come downstream from wider economic factors and changing workforce dynamics.”

Gretchen Boyd, President, NYC House Cleaners:

“From my experience, I can say that the biggest challenge of managing an employee base is the re-engagement of the workforce. There is no doubt that enhancing engagement from employees is definitely a crucial task for any organization however it becomes more difficult after a pandemic. I strongly believe that enhancing the engagement of the workforce requires a highly frequent performance conversation between employees and the organization. As a business leader or a team lead you can try to help your employees to understand how they can contribute to the company’s success or how their work is important for the organization.”

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Andrew Griffith, Founder, Garden Furniture:

“The foremost challenge in managing our workforce will be sustaining high employee engagement and retention… Effectively addressing these aspects is imperative for organizational success, emphasizing the need for strategic initiatives that prioritize employee well-being, growth opportunities, and a workplace culture that fosters motivation and commitment.”

Laurie Hyllberg, Vice President, Kinsa Group:

“In our planning sessions for 2024, a recurring theme is enhancing employee engagement in a hybrid work environment. We’re exploring new technologies and strategies to keep our team connected, engaged, and motivated. Discussions also revolve around refining our performance metrics to better suit our flexible work model. … Moving forward, it’s clear that agility and adaptability will be key in workforce management. Embracing change, being open to new ways of working, and prioritizing the well-being of our team will be crucial as we navigate the uncertainties and opportunities that lie ahead in 2024.”

Phil Strazzulla, Founder, SelectSoftware Reviews:

“In 2024, we aim to enhance our employee experience by focusing on personalized learning and development opportunities. We want to empower our team members to take control of their professional growth, leading to a more skilled and motivated workforce.

George Yang, Founder, Yanre Fitness and OxygenArk:

“By 2024, we need to make sure that every team member feels valued and connected by finding a balance between cutting-edge technology and our core values.”

Andre Kazimierski, CEO, Improovy Painters Chicago:

“I would say my biggest accomplishment in terms of managing my workforce in 2023 was finally instituting a system of regular employee check-ins. This has been something I’ve wanted to do for some time now, but was never able to produce an actionable system for this type of brief one-on-one with employees. This year I made it a priority and now we have a regular schedule in place for checking in with employees, which I hope will go a long way toward boosting employee engagement, increasing employee retention, and overall making my company a great place to work for the people we employ.”

6. Transforming to digital-first operations

The need for robust communication tools and infrastructure to support increased tech adoption and enhanced productivity is a key theme.

Michael Nemeroff, CEO & Co-Founder, RushOrderTees:

“Our initial challenges were around getting everyone up to speed with our digital transformation and keeping our physical team in the loop with any changes that impacted them. Knowing that we’d come out of it as smoothly now would have changed our mental space throughout our transition period.”

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Isla Sibanda, Owner, Privacy Australia:

“Coursing through the ongoing digital transformation as a team was a huge challenge. I wanted to make sure that my employees are equipped with the skills needed for us to become a technology-driven work environment.”

Suzanne Bucknam, CEO, Connecticut Explorer:

“The biggest challenge for me was the rapid pace of technological advancements. Especially in cloud computing and AI, not to mention keeping your top talent happy at their job in a very competitive job market. What made this difficult was finding the right training methods and getting material that suited everybody’s skill level. Thankfully, my team is rather tech-savvy and embraced the training positively, viewing it as an opportunity to expand their skills and adapt to the evolving landscape.”

Max Wesman, Founder & COO, GoodHire:

“In 2023, our biggest accomplishment was implementing and optimizing our technology and collaboration system use in the workforce. 2023 was a big year for us in terms of digital transformation, and we are looking forward to seeing the results in 2024.”

Eugene Klimaszewski, President, Mammoth Security:

“Virtual communication and collaboration can pose hurdles, especially in the security sector where data privacy is paramount. We’ve responded by making significant investments in communication tools and cybersecurity measures to tackle these issues… To succeed in this evolving landscape, it’s crucial to remain innovative, prioritize effective communication, and maintain a strong focus on cybersecurity, ensuring the continued growth and success of remote business operations.”

Hardy Desai, Founder & CEO, Supple Digital:

“With the evolution of AI, many professionals in our industry are worried about losing their jobs and becoming redundant. This year, we’re most proud that we proactively had conversations about those fears with our teammates and used it to bring us closer together. AI may change how our jobs look, but it doesn’t make it any less important for us to maintain the human touch and evolve our team skills to meet those changes. Our team feels valued, supported, and more open to using AI tools to build on their talents, not replace them.”

Will Hatton, Founder & CEO, The Broke Backpacker:

“The integration of AI tools into my operations is going to be one of my biggest challenges in 2024. Many small businesses are using artificial intelligence to recruit and select staff, but the use of AI tools will require me to recruit a technical AI analyst. If I meet my team today, we will talk about how to improve work-life balance, integrating AI tools, and how to improve efficiency in our operations.”

Phil Strazzulla, Founder, SelectSoftware Reviews:

“Our most significant accomplishment in workforce management in 2023 was implementing data-driven HR software that improved talent acquisition and retention. This allowed us to make more informed decisions and create a more efficient recruiting process.

7. Managing productivity

Several leaders mention the importance of understanding and auditing team productivity, especially in remote settings, to maintain or increase labor ROI.

Mark Stewart, Certified Public Accountant, Step By Step Business:

“Effective management was our single biggest accomplishment in 2023 and it involved fostering remote team collaboration, prioritizing employee well-being, and implementing technology for streamlined workflows to enhance overall workforce productivity and satisfaction.”

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Lilia Stoyanov, CEO, Transformify:

“In 2023, our most significant accomplishment in workforce management was successfully implementing a flexible hybrid work model. This not only boosted employee satisfaction but also enhanced productivit by fostering a culture of trust and autonomy, we experienced increased collaboration and innovation within our event management software SaaS team.”

Robert Brandl, Founder & CEO, Email Tool Tester and Tool Tester:

“Experimenting with building in-house writing optimization tools increased our content output velocity without sacrificing quality or editorial standards despite initially lacking extra writers. Technology leveraged existing efforts.”

8. Investing in L&D and growth

Planning and discussions around career development and skills enhancement are emphasized as critical for 2024 strategies.

Robert Kaskel, Chief People Officer, Checkr:

“It’s all about upskilling and focusing on soft skills. We believe that employees with the right blend of soft skills can handle changing technical role requirements that seem to be the norm as technologies evolve so quickly. So we’re looking at how to spot those soft skills, lean into the strong ones, and upskill to improve the weaker ones.

Teresha Aird, Co-founder & CMO,

“To boost our team’s skills through more targeted development. I believe we can further enhance our service by investing in our talent’s growth. And create a more dynamic and innovative workplace to boot.”

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Connor Butterworth, CEO & Owner, Southwestern Rugs Depot:

“Anticipated challenges include staying abreast of the constantly shifting digital landscape to avoid any disruptions in our workflow or connectivity issues that can emerge with a global team. As for current discussions with my team, the key themes are continuous professional development, refining remote work practices, and fostering a learning environment that encourages innovation and flexibility amidst ongoing uncertainties.”

Benzo Lee, Founder, Autoboxup:

“For 2024, we aim to upgrade our employee development programs, targeting the upskilling of 100 employees to meet new technological and market needs. A major anticipated challenge is integrating AI tools in our workforce, ensuring a seamless transition while preserving job security and morale.”

Zarina Bahadur, CEO & Founder, 123 Baby Box:

“In our current planning sessions for 2024, we’re talking a lot about recruitment strategies and how to onboard new members effectively in our hybrid setup. We’re also discussing continuous learning opportunities to keep everyone at the top of their game. The focus is really on sustainable growth while keeping our core values intact.”

Rob Hourie, IT Staffing Specialist, Elwood Roberts:

“We hope to keep our key employees in place and maintain our excellent attrition rate. As me explore new technology, I hope our team takes these changes as an opportunity to upskill and become more skilled. We hope to promote within, we have some managerial roles coming up soon, to relieve stress on management, so seeing people step up to those challenges is an area I’ll keep a close eye on.”

Ben Richardson, Founder & Director, Acuity Training:

“Increase emphasis on upskilling and reskilling initiatives. Adapt to evolving job roles and technologies. It is best to invest in comprehensive learning and development programs.”

Caio Bersot, Communications Manager,

“My biggest hope is to give teammates even more autonomy and opportunities to showcase their work on strategic areas of growth for the business. The idea is to tell people less about how to do something but present them with a project and ask them to find the solutions. This is also part of my biggest challenge for 2024.”

Michael Maximoff, Co-Founder, Belkins:

“Our biggest accomplishment in 2023 was optimizing our training process and streamlining our sales process across the agency. As a thriving B2B agency, we depend heavily on the sales performance and results of our sales teams, and this is something we managed to perfect in 2023. Introducing and mastering new workplace tools has been our biggest challenge in the workforce for a couple of years now, but we’ve gotten really good at implementing new systems and training our workforce to utilize them.”

Vipin Nayar, Founder,

“Our main focus for 2024 is cultivating a culture of continuous learning and upskilling within our workforce… One insight we’ve gained is the importance of fostering a strong sense of community even in a remote setting.”

9. Supporting mental health

Prioritizing mental health and creating support programs for employees is mentioned as a significant aspect of workforce management.

Mark Voronov, Co-Founder & CEO, SocialPlug:

“An essential lesson from 2023 is the importance of mental health and well-being in the workplace. As leaders, we must prioritize this to ensure a healthy and productive work environment.”

Jonathan Rosenfeld, Founder and Managing Attorney, Rosenfeld Injury Lawyers:

“Looking ahead to 2024, our primary aspiration in terms of managing our workforce is centered around enhancing employee well-being, particularly focusing on mental health support programs. Acknowledging the inherent stresses in the legal profession, we are committed to establishing and expanding initiatives that prioritize the mental and emotional health of our team members. This includes implementing counseling services, stress management programs, and fostering an open dialogue surrounding mental health within our workplace. By actively addressing these concerns, we aim to create a supportive and resilient workforce that can navigate the challenges of the legal profession with a stronger sense of well-being.”

10. Establishing DEIB

Striving for diverse, equitable, and inclusive workplaces is a goal for many, with a focus on fostering a supportive and inclusive environment.

Ben Richardson, Founder & Director, Acuity Training:

“I aim for significant strides in fostering diverse, equitable, and inclusive workplaces through data-driven approaches. This could involve leveraging AI to mitigate biases in hiring and promotion. I also plan to integrate monitoring diversity metrics and implementing inclusive policies and practices.”

Max Williams, Founder & CEO,

“Looking ahead to 2024, our goal is to enhance diversity and inclusion initiatives within the team. We plan to implement targeted recruitment strategies, mentorship programs, and training sessions to create an even more inclusive workplace.”

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11. Adapting to change and being agile

Preparing and strategizing for the dynamic and evolving nature of work is ongoing in this fast-changing working world.

Ryan Carrigan, Owner, moveBuddha:

“Our biggest accomplishment was handling the volume that we did with minimal marketing outside of SEO efforts. We didn’t partake in many social media trends, nor did we take an avid interest in video marketing, we just posted blog content and worked to improve our SEO and the business kept coming. I am proud of my team for the hard work they did with minimal preparedness for what came.”

Vladimir Terekhov, CEO, Attract Group:

“Our single biggest accomplishment in 2023 was the successful implementation of a remote-first work policy. We managed to maintain productivity and team cohesion despite the physical distance, which was a significant transition given the previous emphasis on in-office collaboration.”

Christy Pyrz, Chief Marketing Officer, Paradigm Peptides:

*With the pace of technological advancements one of the biggest challenges that we faced was upskilling our workforce to use them. AI, machine learning, and other developments happened at such a fast rate and had such a massive impact on our industry, that maintaining a high level of proficiency in them became imperative for us to be able to create our most effective marketing campaign efforts.*

Billy Parker, Director, Gift Delivery Co.:

“In 2023, our single biggest accomplishment in terms of managing our workforce was our successful implementation of a remote working policy. This allowed us to increase our productivity and efficiency while still providing our employees with the flexibility and freedom they needed to succeed.”

Larry Snider, VP of Operations, Casago:

“Our biggest employee management success for 2023 was a successful transition back to our pre-pandemic systems. Many employees have still remained remote or adopted a hybrid schedule, but overall we have managed to create a schedule that balances the needs of our business and our employees.”

Vlad Khorkhorov, Co-Founder, WebsitePolicies:

“In 2023, our crowning achievement at WebsitePolicies was successfully automating the customization of legal policies using advanced AI algorithms. This innovation enhanced our service efficiency and allowed our legal team to focus on more nuanced and complex client consultations. It was a pivotal moment in marrying legal expertise with cutting-edge technology, greatly benefiting our clients and team.”

What did 2023 look like for you and what’s in store for 2024? Share your own workplace story with us and we’ll work with you to get it published!

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