What does successful selling look like in our new world of AI-generated outreach, automated workflows, and quite a lot of ‘digital noise’?
To find out, we brought together three WiiN-ers and experienced sales leaders for a Women in Incentives Network discussion. We welcome Christine Rodriguez (Cashwave and WiiN Ambassador), Heather Rogers (OC Tanner), and Holly Glowaty (UniFi Group and WiiN Co-Founder).
Drawing on years of frontline and leadership experience, the panel explored what is working in sales today, how technology is changing the profession, and why relationships remain at the heart of commercial success.
Here are the key takeaways from the session.
Top takeaways from the discussion
- Authentic, personalised outreach cuts through in a world of AI haste
- Listening is a skill and most salespeople underuse it. We have two ears!
- AI removes friction, but trust still requires a human
- Discipline and consistency matter as much as talent
- Social selling and personal brand now directly influence pipeline
- Strong sales leaders adapt to the individual, not the process
- Emotional intelligence remains one of the most valuable — and least trainable! skills in sales!
As AI-generated outreach becomes more common, authentic communication is becoming more valuable, not less. Prospects are increasingly skilled at spotting generic messages and the panel was clear that the antidote is specificity.
But, we all love AI time savings. Can we even go back? Simply, yes. That personalisation we know people crave does not need to be complicated. It might be referencing a recent promotion, acknowledging a LinkedIn post, or commenting on a company initiative. As one panelist put it: “Something that separates you from the big blurb that people see on an email or a LinkedIn message.”
Small details demonstrate genuine interest. And genuine interest is what creates the foundation for a relationship. The panel agreed: people want to engage with people, not templates. Use it gently but don’t let a machine pitch for you.
Listening is one of the most underrated skills in sales
During an interactive exercise, attendees were asked to identify the qualities they associate with great salespeople. Empathy, curiosity, honesty, and strong listening skills came up repeatedly, and those themes ran through the entire discussion.
Many sales conversations fail because the seller is too focused on presenting rather than understanding. “Don’t be that salesperson that just vomits up your two-minute spiel of what we do and why we do it,” one panelist observed. Hear hear!
The most effective salespeople create space for the prospect to talk, and then actually listen to what they say and respond. The poor ones have their pitch and want to steer the listener towards it.
The panel also acknowledged how hard this is in practice. When enthusiasm, nerves, or imposter syndrome take over, it is easy to default to proving expertise rather than gathering insight. The quote that says it all?
“Being comfortable enough to sit and take in the information sounds so easy, but I find it to be a very hard thing when you really want to show someone that you get them.”
Understanding comes before selling but this is a skill you can tend to and nurture.
Discipline beats distraction
Sales has always required persistence. What has changed is the volume of competing demands on a salesperson’s time. Years ago things had physical touch points. Now it’s expected in a link.
A strong theme from the discussion was the importance of protecting focus in spite of these demands. “Members of my team literally have emails only, and they won’t respond to anything else during the hour…they’ll go away from everything else and shut it down.”
Without this kind of discipline, the easiest tasks will always crowd out the most important ones. This is a culture shift, but something anyone at any level can try to implement. Boundaries can create opportunities.
Social selling continues to grow
The panel explored the growing role of personal brand and thought leadership in the sales process.
Prospects increasingly research individuals before responding to outreach. They check LinkedIn profiles, review content, and look for evidence of genuine expertise before deciding whether to engage. One panelist described a member of their team who had started posting consistently on LinkedIn and seen a measurable increase in response rates as a result. “If you’re posting on the topic and putting out information that people see as valuable, it is actually impacting response rate.”
Social selling, once seen as a marketing activity, now directly influences pipeline and is an everyone activity. People want confidence that the person contacting them understands their world and a visible, consistent personal brand is one of the most effective ways to demonstrate that before a conversation even begins.
Leadership requires a different skill set
The conversation also touched on what changes when individual contributors move into leadership and the answer is: quite a lot!
Success is no longer measured solely by personal performance. It becomes about creating the conditions for others to succeed. “I really focus on who is selling, and how do I enable them to do it the best way they can for their personality, for their relationships,” one panelist noted. “Not what’s worked for me, it’s looking at the individual.”
The panel also agreed that leading from the front matters. Jumping in on calls, doing the admin, covering when someone is sick. These things earn respect quickly and signal that leadership is not just about telling people what to do.
This was the crux of the session, that relationships still underpin successful sales.
Technology, automation, and AI are reshaping how sales professionals work in terms of tools and process. But trust, authenticity, curiosity, and empathy remain what customers value most.
As Christine Rodriguez closed the session, she shared a quote that captured the mood perfectly: “The companies that will stand out are those that create meaningful experiences and genuine connections with customers and employees.”
The tools will keep always be evolving. The human connection will always remain central.
Thank you to Christine Rodriguez, Heather Rogers, Holly Glowaty, and everyone who joined the discussion and shared their insights.
Would you like to suggest a future topic? Contact us at membership@wiin.global.
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Written by Elaine Keep www.elainekeep.com