Sales isn’t for the faint of heart. But it’s a fairly level playing field where resilience, adaptability, and the ability to thrive under pressure make all the difference.
For Harry Jones, the journey from SDR to Head of Outbound at Second Voice is a testament to these qualities. He’s no stranger to sales or leadership, but his story is one of intuition and openness to growth—taking the skills he already had and learning how to teach them to others. Much like the modern breed of data-driven football managers, many of them ex-players who have the empathy to work with young and unfinished talent, as much as knowing their way around the tactics board on an iPad.
As with many of these new managers, the transition wasn’t without challenges, but it’s clear that Harry has emerged as a gifted leader, transforming not just his own career but also those of the SDRs he mentors.
The early days - Brighton to Barcelona
Harry’s path into sales began in a somewhat unconventional way. He didn’t leave school with high academic accolades; in fact, he admits, “I left education with literally nothing. No A-levels, just a few GCSEs. I didn’t really fit into the educational system.” Like many teenagers unsure of their next steps, Harry found himself pulled into the family business. His father, sensing his son’s lack of direction, put him to work at his recruitment firm.
“I started working for my dad when I was 16, doing all the grunt work—printing CVs, research, you name it,” Harry recalls. Three years later, he was running his own recruitment desk, diving into the world of building products and construction. Recruitment gave Harry a taste of sales, but he wasn’t content to stay in his hometown forever. In 2019, he made the decision to move to Barcelona, lured by the idea of a career in nightlife. As Harry puts it, “I thought I’d move to Barcelona to pursue a dubious career in club promotion—turns out you need money for that!”
When the party lifestyle didn’t pan out, Harry stumbled across an ad for an SDR role at an outsourced sales company. It was there that he got his first taste of the world he’d later thrive in. “I blundered my way through the interview,” he admits, “but luckily, a couple of good managers took a punt on me.”
Back to Brighton for the freelance hustle
Fast forward to 2020, and Harry found himself back in the UK just as the world was shutting down due to COVID-19. Drawing on the skills he’d picked up in Barcelona, he went freelance, working for various companies and building his own clientele. It was during this time that he met Ben Bennett, now the co-founder of Second Voice, through a mutual connection. “We did some projects together, and Ben was great—he helped me out with training and coaching,” Harry says. But it wasn’t until fate intervened that Harry would fully commit to Second Voice.
“I was about to accept a sales manager role at another company,” Harry recalls. “Then, out of the blue, the offer was pulled. Just as Ben was talking to me about Second Voice.” With no other immediate opportunities on the horizon, Harry joined Second Voice, first as a freelancer, and eventually as an integral part of the team.
“I knew about Second Voice before it became what it is today,” he says. “I started on a freelance level, helping Ben with outreach, acting as an SDR, and doing a bit of everything. The first few months were tough, but we got through it.”
Learning on the job and finding the right mentor
Unlike many SDRs who come to the role with little to no sales experience, Harry had already been through the wringer. He’d worked in recruitment, spent time selling in Barcelona, and freelanced for various companies. But despite his background, much of Harry’s sales education was self-taught. “I’ve never really been formally trained,” he admits. “Most of what I know I picked up on the job, through trial and error.”
That said, Harry is quick to acknowledge the importance of good mentorship.
“I’ve had some great managers in the past who taught me valuable lessons, even if it wasn’t formal sales training. And Ben has been a huge part of my learning process at Second Voice.”
One of the most important lessons Harry has learned in sales is that some people are naturally suited to the job, while others aren’t. “I think you need a starting point,” he says. “It’s not about experience, but certain characteristics. You’ve got to be willing to jump in and not overthink things too much.”
For Harry, the ability to embrace rejection is key. “Sales is full of rejection, but if you can ignore that and focus on the rewarding aspects, you’ll thrive,” he explains.
Stepping off the field and into the dugout
After establishing himself as an SDR at Second Voice, Harry transitioned into management, a shift he couldn’t envision would happen so quickly. “Honestly, if you’d told me I’d be managing a team a year ago, I’d have laughed,” he says. “I never thought I’d be in this position, certainly not this early in my career. But here I am.”
One of the biggest challenges Harry faced as a new manager was learning when to step in and when to hold back. “At first, I had a tendency to try and force people to do things by sheer determination,” he admits. “But I quickly learned that people need to find their own way. If I do everything for them, they’ll never learn.”
Now, Harry’s management style is built on trust and autonomy. “I let people make mistakes,” he says.
“It’s not about being perfect all the time, but about learning and improving. If we can get things right 80% of the time and learn from the other 20%, we’re in good shape.”
Harry’s approach to leadership is rooted in teaching, not just telling. “I ask my team why they think something happened rather than jumping in with the answer,” he explains. “It helps them figure things out on their own, and it’s much more effective in the long run.”
Listen first and adapt your training
As an SDR manager, Harry is heavily involved in the hiring process. One of the key qualities he looks for in potential SDRs? The ability to listen. “Sales is a listening game,” Harry says. “If someone’s not paying attention to what the prospect is saying, they won’t get far.”
Adaptability is another trait Harry values, both in his team and in his own management style. “Everyone has their own learning style, so I adapt the training to fit the individual,” he explains. “Some people like to read, others prefer hands-on learning. I build specific training plans around what works best for each person.”
The stats don’t lie
In sales, data is king, and Harry knows it. He uses data not just to track his team’s performance but also to identify trends and refine their approach. “We analyse everything—call data, objections, positive outcomes, you name it,” Harry says. “If I notice that we’re getting through our openers but not closing meetings, I can quickly address that in training.”
But Harry is careful not to overreact to individual data points. “If something happens once, it’s a fluke. Twice, maybe a coincidence. Three times? Now it’s a trend,” he says. “You can’t change your whole strategy based on one bad day.”
Leading on the pitch and from the sidelines
So, how does Harry see himself as a manager? He draws an analogy from his love of football. “I see myself as a bit of a player-manager,” he says with a grin.
“I like to be on the floor with the team, hearing things live as they happen. But I also know when to step back and let them figure things out.”
For Harry, the goal is to create a team that can learn from each other, not just from him. “I don’t want to be the only source of knowledge,” he says. “If they’re learning from each other, the whole team improves.”
Building an Academy to rival Barcelona (or Fulham)?
Harry’s journey at Second Voice is far from over. With a growing team and more SDRs joining the ranks, he’s excited about the future. “I want to see how far we can go,” he says. “Right now, I’m focused on building the team we have and making sure we’re all learning and growing together. It’s not about getting it perfect all the time. It’s about learning, improving, and doing better every day.”
In Harry, Second Voice has not just an SDR Manager, but a leader who’s invested in the growth of his squad and their results. He’s not just setting the tactics, he’s building a team mentality that in itself breeds success, much like the Barcelona football academies of the past (although Harry would argue that his beloved Fulham have also generated a few good youngsters of their own). Here’s to Harry discovering the next Messi (or Ryan Sessegnon).