Select Software, Technology & IT Sales Training Clients
Train for Differentiation, Agility, and Value in a High-Change Industry
Technology selling is no longer about explaining product features — it’s about influencing decision-making in fast-moving, high-stakes buying environments. With more informed buyers, longer sales cycles, and greater internal complexity on the customer side, sellers must bring more than expertise — they must bring perspective.
Richardson helps software, technology, and IT sales teams meet the moment. We empower sellers to build trust quickly, tailor messaging to business needs, and adapt their approach across industries and customer segments. Our training supports high-growth strategies, whether you’re entering new markets, launching innovative products, or enabling virtual or hybrid sales motions.
Why Technology Sales Teams Need a New Approach
Sales professionals in tech and SaaS are navigating heightened pressure from all sides:
- Expanding into new industries with unfamiliar buyer needs and norms
- Long, consensus-driven sales cycles that involve multiple decision-makers
- Buyers armed with more information, options, and pricing transparency
- An iAn increasing need to align solutions with business outcomes, not just features
In this environment, sellers can’t rely on technical expertise alone. They must learn how to connect value to the customer’s world, earn trust early, and shift conversations away from price.
Our Approach to Training Technology Sellers
We believe technology sellers succeed not just because of what they know, but because of how they think, prepare, and connect.
At Richardson, we approach tech sales training by first understanding your go-to-market model, your customer landscape, and your strategic priorities. From there, we design training that builds real-world capability, focusing on skills like insight-led discovery, high-quality deal progression, and virtual or omnichannel selling.
We recognise that different selling motions call for different approaches. That’s why we offer clients a choice between two proven methodologies — Consultative Selling and The Challenger Sale — and work with you to determine which best aligns with your growth strategy, team culture, and customer expectations.
Our goal is to equip your team with the mindset and tools to influence outcomes in a constantly shifting, innovation-driven market.
Sales Training Programmes for Technology Sellers
Richardson helps tech sales teams master 16 critical selling capabilities using modular, blended learning. Programmes commonly leveraged by technology clients include:
The Challenger Sale
For teams aiming to lead with insight, reframe buyer thinking, and take control of high-stakes sales conversations, particularly in saturated or competitive markets.
Consultative Opportunity Pursuit Training
A modern, agile approach to deal progression — helping sellers maintain momentum, adjust tactics, and drive toward next steps with confidence.
Consultative Prospecting Training
Enables reps to identify high-potential buyers, craft compelling messaging, and connect across digital, phone, and social channels.
Consultative Negotiations Training
Builds the skills to shape value perception, defend scope, and close deals that protect margin and enable future growth.
The Accelerate Sales Performance System
Our tech-enabled coaching and measurement platform delivers personalised learning journeys based on real-time performance data, helping teams scale what works.
Outcomes You Can Expect
When your sales team is equipped to lead with insight and respond with agility, you’ll see:
- Higher conversion rates in competitive or complex sales environments
- More consistent sales execution across new or unfamiliar markets
- Improved negotiation outcomes and stronger pricing control
- Faster onboarding and ramp for new sellers
- Clear differentiation based on how you sell, not just what you sell
Supporting Technology Sales Teams in Selling AI
Artificial intelligence is transforming the technology sector — reshaping products, platforms, and business models. From Salesforce embedding AI-driven forecasting into workflows to Okta and Twilio using AI for security and customer engagement, innovation is accelerating. Yet even as adoption grows, many technology buyers remain uncertain. Complex stakeholder ecosystems, unclear ROI, and ethical concerns make scaling AI a challenge.
Richardson and Challenger help technology sales teams navigate this complexity by equipping them to teach buyers how to buy AI responsibly, strategically, and confidently.
Lead the AI Conversation
In an industry where features are table stakes, differentiation comes from insight. Sellers learn to move beyond architecture diagrams and technical demos to lead perspective-shifting conversations that connect AI to measurable outcomes — faster release cycles, improved customer retention, and stronger security. Using Challenger’s commercial teaching approach, sellers reframe AI as a strategic growth enabler, not just a technical enhancement.
Build Buyer Confidence
Tech buyers often include cross-functional stakeholders — from CIOs and CISOs to engineering and finance leaders. Through Richardson’s Consultative Selling framework, sellers learn to empathize with uncertainty, address integration and compliance risks, and guide buyers through ambiguity. They become trusted advisers who simplify complexity and provide clarity in a crowded market.
Create Constructive Urgency and Define Outcomes
Standing still feels safe, but it’s costly. Sellers learn to quantify the business impact of inaction — slower innovation, missed revenue opportunities, and increased competitive risk. By aligning AI outcomes to clear business metrics such as reduced churn or higher NPS, sellers help buyers see the commercial value of adoption.
Sustain Success
Through the Accelerate Sales Performance System, sales leaders can reinforce AI-specific skills with data-driven coaching, sustainment tools, and analytics that ensure consistent execution across every customer interaction.
The result: Technology sales teams become navigators — not just product experts — who help buyers move from hype to clarity, building confidence in every AI decision.
Success Story: Fortune 500 Computer Manufacturer
A major global technology company needed to increase direct sales, improve cross-sell performance, and strengthen relationships in a large, multi-division call center.
Partnering with Richardson, they implemented a blended learning solution informed by stakeholder interviews. Training focused on:
- Keeping conversations
- Upselling and positioning complementary products
- Understanding how buyers make decisions
- Recognising and acting on buying signals
- Resolving objections and managing tough conversations
The results:
- $321 in revenue generated for every $1 spent on training
- 10% average increase in weekly margin
- Over $5 million in margin gains post-training
FAQ: Richardson's Technology Sales Training Solutions
Q. What is technology sales training?
A. It’s training designed for software, IT, SaaS, and tech sellers who need to engage complex buying teams, sell solutions in business terms, and win in competitive or disrupted markets.
Q. How does Richardson customise tech sales training?
A. We interview stakeholders, assess performance gaps, and design programmes based on your GTM strategy, product complexity, and customer base — from SMB to enterprise.
Q. Can we choose between Consultative and Challenger methodologies?
A. Yes. We help you determine which methodology aligns best with your sales strategy and market dynamics. Both options are available — and distinct.
Q. Is Challenger a good fit for SaaS and IT sales teams?
A. Very much so. Challenger helps sellers drive urgency, shift buyer thinking, and compete on value — especially in high-growth or commoditised categories.
Q. Do your programmes support virtual and hybrid selling environments?
A. Yes. We offer programmes specifically designed to build skills in digital prospecting, remote engagement, and omnichannel selling across complex sales cycles.
Q. Why do technology sales teams need AI-specific training?
A. AI is changing how technology buyers evaluate value. Sellers must help clients move beyond feature comparisons to business outcomes. Richardson and Challenger equip sales teams with the frameworks to guide multi-stakeholder decisions, clarify ROI, and build confidence in AI investments.
Q: How can sellers build buyer trust when selling AI in technology?
A. Trust is built through clarity and confidence. Sellers learn to simplify complexity, frame AI adoption as a strategic advantage, and address concerns about security, compliance, and integration. With insight-driven teaching and consultative skills, they help buyers navigate uncertainty and act decisively.
