Sales Ridealong 101: A Comprehensive Guide

Road trips are always fun. But what if you could take the “road” with you? If you think you know sales ridealongs, buckle up — because they just got a digital makeover.

The future of field sales coaching is virtual and uses AI to deliver smarter, faster performance notes and feedback for your reps. You can still ride shotgun with your team members but from the comfort of your office, home, or local coffee shop. Through virtual ridealongs, you can make every sales interaction an opportunity for growth — all without leaving your desk (or couch or weirdly expensive bean bag chair).

Pull up and discover sales ridealong basics, how ridealongs work, and why they’re important. Then, switch gears and learn three best practices for taking (and coaching) successful field sales calls.

What is a Sales Ridealong?

A sales ridealong is a practice in which a field sales manager joins a sales rep during a customer engagement or interaction, and observes and guides the rep with the goal of improving their sales process. 

Traditionally, sales ridealongs were done in person, face-to-face — but Rilla has modernized this concept by facilitating virtual ridealongs. Virtual ridealongs allow sales managers to coach reps remotely by utilizing AI to record and analyze rep conversations with customers. This not only boosts training efficiency, but opens the doors to new possibilities like long-distance coaching.

How Do Sales Ridealongs Work?

Before making the virtual jump, sales ridealongs typically involved a more senior salesperson or manager accompanying a rep — literally “riding along” in the car — to meet with existing or potential customers. This hands-on approach made it possible for the more senior sales professional to study the customer interaction and provide immediate feedback for the rep. 

The goal of sales ridealongs is to mentor the rep and increase their potential for sales. This is how the process works:

• Preparation: Before the ridealong, the manager and rep might discuss the day’s goals, client specifics (e.g., website, Facebook page, or Zillow profile), and any particular focus areas (e.g., financing, discounts or promos).
• Observation: During the customer interaction, the sales leader quietly watches and listens to the rep’s approach, communication with the customer, and inclusion of any relevant or timely information.
• Feedback: After each customer visit or at the end of the day, the manager or senior member can debrief with the rep during a coaching session. Effective feedback includes praise or acknowledgment of observed successes and constructive criticism about areas that need improvement. Managers may also suggest role-playing scenarios so reps can practice handling specific situations. Occasionally, sales managers will even take over the rep’s sale if they’re not able to close the deal. This helps to demonstrate to the rep how they can handle similar scenarios in the future.
• Development: Using the insights gained from the ridealong, managers can suggest ongoing education for their reps and tailor their training initiatives to reps’ individual needs.
• Follow-up: Managers may schedule subsequent ridealongs or meetings to review reps’ progress on their feedback and action items. This helps to ensure consistent improvement to their sales performance.

And now, with tools like Rilla, managers can turn this once-strictly-IRL event into a highly effective virtual coaching and mentoring process. The beauty of this is that it still fosters a supportive learning environment, and it can immediately address gaps in reps’ sales techniques.

Why are Sales Ridealongs Important?

Sales ridealongs are important because they help managers observe and enhance their reps’ sales techniques based on real-life customer conversations. It’s not coaching based on hypotheticals or “example” situations — it’s coaching rooted in genuine client interactions.

Benefits of ridealongs include:

• Contextual coaching: Managers can provide feedback and training about reps’ literal sales performances rather than imagined scenarios. 
• Immediate (potential) improvement: Although it’s up to reps to “walk the walk,” managers can provide instant feedback so nothing gets forgotten or slips through the cracks.
• Sales rep autonomy: Since managers simply observe and don’t overtake the sales process, they help reps develop confidence and trust in themselves, which are crucial components for growth and autonomy in closing deals.

Ridealongs help managers foster a proactive learning environment that provides the foundation and educational reinforcement sales reps need to perform their best. 

3 Best Practices for Sales Ridealongs

These days, sales coaching can be done from just about anywhere with a wifi connection. Tools like Rilla help managers up their reps’ game, instill confidence, and provide feedback without the pesky car sickness or exorbitant gas prices.

Discover three best practices for successful sales ridealongs and discover why “virtual” is the way of the future.

1. Extend Your Sales Coaching Reach Virtually

Although in-person practices can still be effective, you can extend your coaching reach by taking advantage of virtual ridealongs. This eliminates the need for physical travel — saving time and organizational budgets — and increases coaching opportunities. With virtual ridealongs, managers can provide real-time feedback that helps reps close deals, increase ticket sizes, and feel more confident in their abilities. And because of how time-consuming physical ridealongs can be, it’s often impossible to coach your whole sales team at scale. Virtual ridealongs allow you to coach every appointment, every time.

2. Tailor Coaching and Enhance Sales Strategies with the Help of AI

Virtual ridealong software can provide AI-driven insights about sales conversations that allow managers to customize their coaching to the individual rep. By analyzing interactions between reps and customers, and deep-diving into sales engagements, tools like Rilla help managers provide evidence-based feedback that lets reps take real action. This practice supports the setting and tracking of measurable goals, which allows sales teams to refine their strategies as needed.

3. Mind the Market’s Needs and Remain Relevant

When you use a tool like Rilla, you’re equipped with AI’s power to detect market changes — so you can quickly align your sales approach with economic and cultural demand. When you adapt your sales training based on the market’s conditions and your organization’s needs, you can ensure your feedback remains timely and relevant. AI-powered tools like Rilla help sales teams meet their target audience’s unique challenges and close deals more effectively.

Rilla is Your Best Sales Copilot

Embracing tools like Rilla means stepping into the future of sales coaching. And in this future, physical proximity is no longer a factor in whether or not a manager-rep feedback session is successful. Through AI analytics and insights, Rilla can turn every sales interaction into a data-driven teachable moment that helps your reps close deals and boost ticket sizes.

Once you’re ready to create new sales opportunities and accelerate your team’s growth, Rilla is with you in the passenger seat (metaphorically — you no longer need anyone there in-person, remember?). Contact us today to book a demo.