Mastering H2H Sales in Tech: Empathy, AI, and Feedback
Bart Kowalczyk, the founder of AutomateNow, is in conversation with Adrian Chiriac, Sales Team Lead and Principal Account Executive at HubSpot, discussing whether sales is the most challenging job in the tech industry today.
The Importance of Human-to-Human Sales in Tech
In the rapidly evolving world of technology, the significance of human-to-human (H2H) sales cannot be overstated. While business-to-business (B2B) and business-to-consumer (B2C) models have their place, H2H sales focus on building genuine relationships. This approach emphasises understanding clients' needs, fostering trust, and creating meaningful interactions that go beyond mere transactions. In tech sales, where products and services can be complex, the human touch ensures that clients feel valued and understood, leading to stronger, long-term partnerships.

Integrating Empathy into Sales Strategies
Empathy is at the heart of H2H sales. It involves putting oneself in the client's shoes, understanding their challenges, and addressing their concerns with genuine care. In tech sales, this means recognising the unique pressures clients face, such as tight deadlines, budget constraints, and the need for innovative solutions.
Adrian said:
By actively listening and responding with empathy, sales professionals can tailor their approach to meet specific client needs, fostering a sense of trust and collaboration. This empathetic approach not only enhances client satisfaction but also differentiates a company in a competitive market.
Leveraging AI for Enhanced Productivity
AI has revolutionised many aspects of business, and sales is no exception. When used effectively, AI can enhance productivity by automating routine tasks, analysing vast amounts of data, and providing actionable insights. For instance, AI can summarise lengthy email threads, allowing sales professionals to quickly get up to speed on client communications. It can also provide data-driven insights that help in crafting personalised sales pitches. By reducing the time spent on administrative tasks, AI enables sales teams to focus on what they do best: building relationships and closing deals.

The Critical Role of Feedback and Reflection
Continuous improvement is vital in the dynamic field of tech sales. Feedback and reflection play crucial roles in this process. Sales professionals should actively seek feedback from clients and colleagues, using it to refine their strategies and improve their performance. Reflecting on past interactions, both successful and unsuccessful, helps in identifying strengths and areas for improvement. This iterative process of feedback and reflection ensures that sales approaches remain effective and aligned with client needs, ultimately leading to better outcomes and higher sales targets.
Implementing Joint Evaluation Plans for Success
For complex deals involving multiple stakeholders, a structured approach is essential. Adrian suggested to work on joint evaluation plans (JEPs) A JEP outlines all necessary steps, working backwards from the implementation date to ensure that all requirements are met. This includes addressing security concerns, pricing discussions, demos, and Q&A sessions. By involving all stakeholders in the planning process, JEPs ensure that everyone is aligned and accountable. This collaborative approach not only streamlines the sales process but also builds trust and transparency with clients.
Balancing Problem Solving with Hitting Sales Quotas
One of the most significant challenges in tech sales is balancing the need to solve client problems with the pressure to hit sales quotas. While it is essential to meet targets, focusing solely on numbers can lead to a transactional approach that undermines long-term relationships. Instead, sales professionals should prioritise understanding and addressing client issues, positioning themselves as trusted advisors. This problem-solving mindset, combined with a strategic approach to hitting quotas, ensures that sales efforts are both productive and sustainable. By aligning client success with sales targets, companies can achieve their goals while maintaining strong, lasting relationships with their clients.
RELATED ARTICLES
Why Opt for the Sales Demo Call Stage in HubSpot?
Bart Kowalczyk of AutomateNow asked Emma McCarthy, Channel Account Manager for HubSpot, based in Dublin, for her top tips.
Get inspired
AI-Driven Human-Centric Sales and Marketing | H2H Sales Podcast
Bart and Anna attended the Inbound 2024 conference in September, where they conducted insightful interviews to share their learnings on leveraging AI ...
Get inspired
What if Your Best Sales Tool Isn’t AI?
During the INBOUND conference in San Francisco, Bart Kowalczyk, host of the H2H Sales Automation Podcast, sat down with Sarah McDevitt, Senior ...
Get inspired
Mastering International Sales with Human-Centric Approaches
Behind every HubSpot pipeline, there’s a story. In this short podcast interview with Alan Graham, you’ll hear how digital transformation and ...
Get inspired
From Growth to Grit: How HubSpot Agencies Are Preparing for 2026
This episode of the H2H Sales Automation Podcast was recorded live in London during the GROW Europe event. Host Bart Kowalczyk, CEO of AutomateNow, ...
Get inspired
Being Human in the Age of AI: A Conversation with Kyle Jepson
When I sat down with Kyle Jepson, HubSpot’s evangelist and the voice so many of us know from HubSpot Academy, the atmosphere was electric. We’d just ...
Get inspired
How to Grow in Challenging Times by using CRM
Bart Kowalczyk of Automatenow asked Stephanie Robinson, Business Growth Coach & Build-Up Entrepreneur, for her advice. Stephanie Robinson is the ...
Get inspired
How to Get your Sales Content Right
Bart Kowalczyk, MD of AutomateNow and Leslie Douglas, VP of Membership and GTM Strategy at Sell Better by JB Sales.
Get inspired
When Your Lead Becomes Sales-Qualified in HubSpot?
Bart Kowalczyk of Automatenow asked Stuart Lotherington, Managing Director of SBR Consulting in London, for his perspective.
Get inspired
What's New in HubSpot for 2025: A Sneak Peek
As we enter 2025, Bart, the founder of AutomateNow HubSpot Agency, has released a brief podcast episode to explore the upcoming developments in the ...
Get inspired
How you can Connect Linkedin and HubSpot?
Before David Chevalier co-founded Leadjet (which became Surfe), he had a career in the financial industry. How he ended up there is a story in itself.
Get inspired
ERP + HubSpot: The Revenue Playbook
How real companies connect their systems, reduce chaos, and create a single customer journey.
Get inspired
CPQ at HubSpot: How AI Is Speeding Up Quotes and Closing
On the H2H Sales Automation Podcast, host Bart Kowalczyk (CEO, AutomateNow) sits down with Ethan Copit, Group Product Manager for HubSpot CPQ ...
Get inspired
HubSpot: Mastering Business Process Automation
In this conversation, Bart interviews Sam Easton, a project manager at AutomateNow, about mastering sales and other business processes in HubSpot. ...
Get inspired
Is HubSpot Implementation Worth the Investment? | AutomateNow
Helping us deep-dive into the world of HubSpot enablement is our very own Steven Tomlin one of our key sales gurus at AutomateNow. In this post we ...
Get inspired
Unlocking Startup Success: Actionable Insights from Eoin McGuinness
As a community of business owners, startup founders, and entrepreneurs, we're always on the lookout for strategies to propel our businesses forward.
Get inspired
Stop Selling, Start Disqualifying to Win
We’re dropping a brand new episode of the H2H Sales Automation podcast this week, and trust us, you’ll want to tune in.
Get inspired
Marketing Automation for SaaS: Smart Platforms, Awesome Content and Human Processes
Marketing Automation for SaaS: Smart Platforms, Awesome Content and Human Processes What exactly is marketing automation, and why is it so critical ...
Get inspired
Stop Spamming, Start Selling: Redefining Leads with Surfe
In the latest H2H Sales Automation Podcast, Bart Kowalczyk, CEO of AutomateNow, sits down with Marta El Bay, Head of Partnerships at Surfe, to ...
Get inspired
How to grow by 50% in 2025 with HubSpot
In today's rapidly evolving business landscape, leveraging technology is no longer optional—it's essential. As we look towards 2025, businesses must ...
Get inspired
Unlocking CRM Potential: Mastering HubSpot's New Data Model
Understanding the New HubSpot Data Model HubSpot's latest data model update paves the way for a more efficient CRM experience, enabling users to more ...
Get inspired
