Rob Dwyer: From “Just a Job” to a Lasting Career in Support

Welcome to Escalations, a series where I’ll be sharing stories of some amazing careers that started in Customer Support. While many of these will be compiled into a book, I will also be regularly sharing stories here, too. If you like this content, please consider subscribing or sharing. 

Introduction: The Starting Point

Rob Dwyer began his career in support out of necessity rather than a grand plan. In 2009, he walked into a Convergys contact center in Arnold, Missouri, simply needing insurance and a steady paycheck.

Despite the humble beginning, Rob’s curiosity and willingness to learn soon propelled him from taking phone calls to building training programs, overseeing quality assurance, and ultimately leading customer engagement as a company executive.

The Growth Path

Not even a year after starting as a frontline retention agent, Rob was offered a training role—an opportunity that required him to step out of his comfortable routine of working from home. From there, he embraced every chance to solve new problems, even if it meant tackling unfamiliar challenges like curriculum development, launching remote training programs, or managing a growing quality team.

His journey at Convergys evolved into a global coaching role, where he’d travel extensively to various sites, observe team leaders, and guide them on performance and coaching methods. Later, at Customer Direct, he built an entire training department from scratch, selecting software tools, implementing a learning management system, and overseeing quality—ultimately proving his ability to juggle diverse responsibilities.

Implementing This in Your Own Career

• Offer to help on unfamiliar projects to gain visibility and new skills.
  

• Recognize when to sacrifice comfort (like remote work) for long-term growth.
  

• Build on successes—small wins can lead to bigger opportunities.
  

Breaking Through: Lessons & Key Decisions

1. Take Calculated Risks

Rob was never content to stay where he was comfortable. He said yes to new positions even if it meant more travel, a longer commute, or a shift from hourly to salaried with no overtime. By doing so, he demonstrated to leadership that he was open to growth and willing to adapt.

How You Can Apply It

• Embrace roles that stretch your abilities, even if they come with temporary downsides.
  

• Negotiate for fair compensation while remaining flexible on responsibilities.
  

2. Become a Problem-Solver

Working in retention taught Rob to dig beneath the surface of every problem. Instead of just accepting “I want to cancel,” he probed for the root cause and used his knowledge of products and policies to present better solutions. This same approach now guides him in customer engagement and sales.

How You Can Apply It

• Ask clarifying questions to discover the real reason behind a request.
  

• Present solutions that meet genuine needs, not just surface demands.
  

3. Build Meaningful Relationships

Rob frequently mentions how relationships—and the trust they foster—led to invitations for new roles. He reached out, offered to help in areas outside his direct responsibility, and actively sought feedback, becoming a known problem-solver and team player.

How You Can Apply It

• Offer genuine support to peers and leaders, even on projects outside your official job description.
  

• Ask colleagues for feedback to show that you value their expertise and want to improve.
  

4. Stay Willing to Learn

Throughout his career, Rob has stepped into uncharted territory—managing quality teams, selecting software, or leading product launches. Each pivot required new skills, sometimes learned on the fly, as he balanced his existing workload with learning opportunities.

How You Can Apply It

• Continuously identify gaps in your skill set and find ways to fill them—online courses, mentorship, or hands-on projects.
  

• Treat each new role or project as a chance to expand your expertise and demonstrate versatility.
  

5. Stand Out with Authenticity

Early on, Rob became known as “the guy with the cufflinks,” a small but memorable personal brand. Beyond that, he found unique ways to connect with people—Lego collections, personal interests, and other authentic touches that helped him network across different teams and departments.

How You Can Apply It

• Look for genuine personal traits or hobbies that can spark conversations and relationships.
  

• Maintain a consistent professional image that aligns with your values and personality.
  

Actionable Takeaways

• Seek Opportunities Beyond Your Comfort Zone
  Challenging tasks and unfamiliar roles often force you to learn quickly. By stepping up, you prove your flexibility and enthusiasm for growth.
  

• Focus on True Customer Pain Points
  Success in support depends on uncovering the deeper issues behind a request. Honing these diagnostic skills is valuable in any department.
  

• Strengthen Internal & External Relationships
  Collaborate with peers, offer your assistance, and share insights. This builds trust, making you the go-to person when new roles or projects arise.
  

• Turn Feedback Into Growth
  Actively seek critiques on your work and leadership style. Implementing suggestions shows others you’re serious about evolving and taking on more.
  

Where They Are Now & Final Words of Advice

Today, Rob holds a senior leadership role bridging both a contact center operation and a SaaS platform, overseeing sales, marketing, customer success, and more. His story shows how remaining open, curious, and persistent can transform a short-term “job” into a meaningful, long-term career.

Do you have a story to tell or insights to share? Consider having a conversation with me so I can share something like this about you!