Successful software business leaders invest in sales and marketing because they recognize these functions as enabling the company’s ability to grow, remain competitive, and earn a profit. When businesses don’t invest enough in sales and marketing, they can miss out on many opportunities – among them being revenue generation, building brand visibility and recognition, and opportunities for customer acquisition and retention.
Jaclyn Jagodinski operates on this belief as the Vice President of Sales and Marketing at AssetWorks Fleet and Enterprise Asset Management, where she is known for turning innovative ideas into impactful results. Over her tenure, she has built high-performing teams, aligned sales and marketing efforts, and prioritized customer-centric strategies to drive success.
Jaclyn’s leadership blends strategic vision with hands-on execution, ensuring that initiatives deliver measurable outcomes. Passionate about collaboration, she fosters alignment across teams and leverages data-driven insights to deliver exceptional value. Beyond her professional achievements, Jaclyn is a mentor dedicated to empowering others, exemplifying leadership grounded in integrity and relationship-building.
Can you share your journey to becoming Vice President of Sales and Marketing at AssetWorks Fleet and Enterprise Asset Management? What key milestones helped you reach this role?
My journey to becoming Vice President of Sales and Marketing at AssetWorks has been both challenging and deeply rewarding. It started with a strong foundation in marketing strategy, ROI reporting and strategic communication, which I honed early in my career. Over the years, I focused on mastering the art of connecting our team to our customer needs and supporting our innovation with various process and product solutions, which became a key differentiator in my approach.
Several milestones shaped my path to this role. One was supporting the growth of the sales and marketing division by recognizing the unique talents of our team members and building the team to support our overall sales and business growth. Over this time period that not only exceeded sales targets but also brought our sales and marketing teams into closer alignment.
Finally, mentorship played a critical role. I was fortunate to learn from leaders and peers who encouraged me to think strategically and push boundaries. As a result, I’ve always sought opportunities to combine data-driven decision-making with creativity, which has been instrumental in my progression to this role.
How do you balance strategic planning with hands-on execution in your dual role overseeing both sales and marketing?
Balancing strategic planning with hands-on execution is a daily commitment to prioritization and focus. I believe the key lies in setting a clear vision and aligning all activities with overarching business objectives. At AssetWorks we dedicate time to strategic planning by continuously evaluating market trends, customer feedback, and competitive dynamics. We do this in collaboration with our marketing team, industry experts and sales team. This allows us to identify opportunities and ensure our teams are equipped with the right tools and strategies.
At the same time, I stay actively involved in execution to remain connected to the pulse of the business. This often means collaborating on key campaigns, engaging with clients through events and our user conference, and working with sales team members to understand their individual challenges. I’ve found that this dual involvement not only keeps strategies grounded but also inspires trust and confidence within the team.
Ultimately, it’s about empowering others. I rely on a strong team of leaders in both sales and marketing who are skilled at executing the vision we set together. This ensures we maintain momentum while keeping an eye on the bigger picture.
We measure the success of our marketing mix by tying clear KPIs to business outcomes, like lead quality and ROI, and monitoring performance in real-time. To stay ahead of changing market conditions, we adapt by conducting market research, testing new strategies, and using feedback to refine our approach.

What advice would you give to someone aspiring to lead both sales and marketing in a competitive industry?
My advice to leaders is to build strong relationships which can result in developing a unified vision. When you build a team of individuals who can rally around a shared goal you will see tremendous growth. With that growth it is important to not lose sight of your customers and your overall mission which is to build trust and integrity in the market you service and add value to your customers. Finally, empower your team in the process. Leadership doesn’t mean that you do it all, creating a culture of accountability and recognition will take you much further.
Alignment between sales and marketing is built on shared goals, open communication, and a commitment to understanding our customers’ needs. By uniting around common metrics and fostering collaboration, we ensure both teams contribute to driving growth and delivering value effectively.
The AssetWorks Academy is AssetWorks’ annual software user conference, designed to bring high value to customers through hands-on training, 125+ unique classes, networking opportunities, and so much more. How do you approach planning and executing such a comprehensive training and networking program?
Planning and executing the AssetWorks Academy requires a blend of strategic vision, organization, and a deep understanding of client’s needs. Here’s how we approach it:
- Define clear objectives: The first step is to establish what we aim to achieve—Our event is a premier training event, and we aim to be the best in the industry. We set KPIs around this for attendance, customer satisfaction and course establishment.
- Understand the audience: We invest time in gathering feedback from past attendees and engaging with customers to understand their expectations and pain points. This ensures that the content is relevant, actionable, and tailored to their needs. We recently engaged a customer advisory board which has been crucial in the success of planning for this upcoming year.
- Content design and delivery: The program is built around a mix of training sessions, hands-on workshops, and panel discussions led by experts and customers. We strive for a balance between technical depth and practical application, ensuring attendees walk away with new skills and strategies they can immediately apply.
- Collaboration across Teams: Planning the Academy is a cross-functional effort. We work closely with our professional services, product, sales, marketing, and customer success teams to develop the agenda, secure speakers, and ensure consistent messaging throughout the event.
- Engaging networking opportunities: Beyond training, networking is a key value driver. We create opportunities for attendees to connect through breakout sessions, roundtable discussions, and informal social events. These moments foster community and spark valuable conversations.
- Technology and logistics: Seamless execution is critical. From venue selection and event technology to attendee registration and post-event surveys, we focus on ensuring a frictionless experience for all participants.
- Continuous improvement: After the event, we gather feedback and analyze attendee engagement metrics to identify areas for improvement. This commitment to iteration helps us raise the bar every year.
Ultimately, the success of the AssetWorks Academy lies in its ability to deliver value, build relationships, and reinforce our position as a trusted partner. I am lucky to work with an incredible planning team that ensures the event continues to be a highlight for our customers and a key driver of engagement.
What’s your go-to way to recharge after a busy week at work?
After a busy week, I find it essential to step away and refocus my energy. This means spending valuable time with family and friends. I have two small children and an incredible network of people around me who support my personal and professional goals, so this is our time to reconnect. I also dedicate time to hobbies that help me relax, like time at the gym, cooking and enjoying the outdoors. However, my favorite place to recharge is on the beach!