Introduction: a people-first approach to outbound sales
Isaiah Harrison didn’t start his career with a headset and a quota. He started on the field, working in marketing for the Denver Broncos. From there, he pivoted into insurance sales, before eventually landing in SaaS as an Enterprise BDR at Contentful, a leading digital experience platform that helps modern businesses meet the growing demand for engaging, personalized content at scale. By blending composability with native AI capabilities, Contentful enables dynamic personalization, automated content delivery, and real-time experimentation, powering next-generation digital experiences across brands, regions, and channels for more than 4,200 organizations worldwide.
At first glance, it’s a winding path. But for Isaiah, each step revealed something bigger: his real motivation isn’t competition or numbers on a board. It’s people.
“I love seeing others succeed. People are what is most motivating for me,” he shares.
That focus on people has guided his journey from an individual contributor into management. Today, as the leader of Contentful’s Enterprise Outbound BDR team, Isaiah is showing how smarter outbound goes beyond data and tools. It’s about encouragement, collaboration, and keeping outreach human.
From sports to SaaS: Building a career in enterprise sales leadership
When Isaiah joined Contentful as an Enterprise BDR, there wasn’t a set path from his role into management. Instead of waiting for one to appear, he created it himself.
He started by building a track record of success in the role. Then he doubled down by enrolling in an MBA program at Grand Canyon University while still working full-time. Balancing quotas and coursework wasn’t easy, but it gave him clarity about his motivation and sharpened his focus on people-first leadership.
“Because of Contentful’s unique environment for growth and progression, an opportunity came.”
At the same time, Isaiah was intentional about networking internally. He sought out conversations with stakeholders across the business to understand what leadership required and how he could prepare for it. Within 20 months of starting, he stepped into management, proof that growth at Contentful is as much about initiative as opportunity.
Building a high-performing BDR team
When Isaiah moved into a leadership position, he saw an opportunity to unlock the full potential of the Enterprise Outbound BDR team and guide them toward greater success.
He started by focusing on hiring smart. Partnering with recruiting and other managers, Isaiah helped create an ideal candidate profile and was deliberate about bringing in the right people, not just the first people available.
Then he doubled down on encouragement. For Isaiah, encouragement isn’t just a morale booster; it’s also a tool for accountability.
“The best managers know when to lift you up and when to challenge you. Encouragement, done effectively, can be leveraged to do both,” he explains.
By understanding how each rep received feedback, he used encouragement to motivate, reset, and push his team forward.
The results were clear. In just one year, the team transformed from finding their rhythm to exceeding expectations and achieving new levels of success.
Collaboration across teams: How enterprise outbound sales thrives at Contentful
Breaking into enterprise accounts takes more than cold calls and emails. For Isaiah’s team, success comes from collaboration across the business.
When prospect intent signals show up, there’s often a two-month window before a meeting is booked. During that time, outbound reps are reaching out by phone, email, and LinkedIn. But that’s rarely enough on its own.
That’s where marketing, partnerships, and operations come in. Coordinated campaigns, events, and account planning make the team’s outreach “too loud to ignore.” By aligning across departments, Isaiah ensures his BDRs aren’t knocking on doors alone. They’re part of a broader, multi-threaded effort that dramatically improves success rates.
This cross-functional approach doesn’t just drive meetings. It also models a key lesson for modern outbound sales: when teams work together, customers don’t just hear from a vendor. They hear from a partner.
Personalization and AI in outbound sales
For Isaiah, outbound success isn’t about sending more messages — it’s about sending better ones. His team has embraced a modern, data-driven approach that combines personalization with AI to reach the right people at the right time.
Rather than relying on high-volume outreach, they’ve shifted their focus toward meaningful engagement — crafting outreach that speaks directly to enterprise customers’ needs and challenges. The result? More authentic conversations and stronger connections.
Still, Isaiah emphasizes that personalization alone isn’t enough. “Even with perfect messaging and the right contact, if an account isn’t ready to buy, the effort won’t land,” he explains. Intent must always lead the way.
The takeaway for sales teams: use AI to streamline repetitive work, rely on data to guide timing, and keep human creativity at the heart of every message. That balance is what keeps outbound strategies relevant — and effective — in a fast-changing market.
Sales culture that drives growth and career development
Behind every strong outbound strategy is a culture that keeps people motivated. At Contentful, that culture goes beyond quotas and dashboards.
Isaiah points to resources like an education budget and volunteer time off (VTO) as signals that the company invests in people, not just performance. BDRs aren’t limited to a single track, either. Over the past year, team members have launched careers in marketing, partnerships, account management, sales management, and beyond.
For new reps, seeing that kind of mobility is inspiring. It creates a cycle of motivation: they show up with the right attitude, do their current role with excellence, and know that growth is possible if they put in the work.
In Isaiah’s words, it’s an environment that “fosters a special career at Contentful autonomously.” And that culture helps individuals to thrive and it strengthens the entire outbound organization.
Actionable outbound sales strategies for BDRs and leaders
Isaiah knows outbound isn’t a one-size-fits-all formula. What works one quarter might not work the next — and that’s why creativity and adaptability are so important.
Here are his top strategies for BDRs and sales leaders looking to level up their outbound efforts:
- Stay creative and flexible. Outbound is “more art than science,” Isaiah says. Don’t get stuck in a single playbook. Experiment with new tactics and adjust when the market shifts.
- Balance automation with personalization. Let AI streamline the repetitive tasks so reps can spend more time personalizing outreach to the right people at the right accounts.
- Listen to your reps. The best insights about what’s working — and what isn’t — come directly from the people on the front lines. Creating space for feedback not only improves strategy but also fuels personal growth on the team.
For Isaiah, this mix of flexibility, data, and human input is what keeps outbound strategies resilient and effective.
Looking ahead: The future of outbound sales
Isaiah is optimistic about where outbound is headed. With AI, intent data, and automation, prospecting has never been more efficient. But the real opportunity lies in how teams use those tools.
“The future belongs to teams that master the balance, using technology to scale, while keeping outreach authentic and human,” he says.
For enterprise customers, that balance is what separates a vendor from a true partner. Buyers don’t just want another email in their inbox. They want to engage with someone who understands their challenges and can help solve them.
At Contentful, Isaiah is excited to keep building a team that embraces innovation without losing the human touch. Because in the end, smarter outbound isn’t just about efficiency. It’s also about connection.
Finding growth through community
Isaiah’s story shows that outbound success isn’t just about hitting numbers — it’s about building people, teams, and connections that last. From creating his own path into leadership to experimenting with new strategies, his journey reflects a bigger truth: growth happens when you combine creativity with community.
For BDRs and sales leaders, that means leaning on peers, mentors, and the resources around you. And for companies, it’s about creating cultures that make growth possible.
Interested in working for a company that helps you find time for what matters most to you? Check out Contentful’s job openings here.
