Ran Oelgiesser of RightBound: How To Be Great At Sales Without Seeming Salesy

Authority Magazine
Authority Magazine
Published in
9 min readNov 3, 2021


There’s nothing wrong with being passionate about what you sell — in fact, the message your sales team should be conveying is that your product will undoubtedly change your prospect’s life for the better. If this is construed as “pushy” or “salesy” — so be it. If your product doesn’t meet your prospect’s needs, say so and then move on.

As a part of my series about how to be great at closing sales without seeming pushy, obnoxious, or salesy, I had the pleasure of interviewing Ran Oelgiesser.

Ran Oelgiesser is the co-founder and CEO of RightBound and is a serial entrepreneur who had his first company acquired by Microsoft. Originally a software developer, Ran spent most of his career leading go-to-market strategy for fast-growing startups and building robust sales and marketing teams. His hands-on sales experience inspired him to create the sales revolution he is leading: removing the “heavy lift” of outbound Sales Development by intelligently automating prospecting and outreach.

Thank you for doing this with us! Before we dig in, our readers would like to learn a bit more about you. Can you tell us the “backstory” about what brought you to this career path?

I was a co-founder of a startup rather early in my career. After my first startup was acquired by Microsoft, I spent the next ten years leading marketing and sales teams for different companies until the entrepreneurial bug hit me again. When Rotem Dafni suggested we build an autonomous prospecting platform, I immediately knew that this was the real deal and we decided to found RightBound together. Having worked in sales for many years, I had experienced first-hand the need for such a solution and was ready to make it happen. Two years later I’m happy to report that RightBound is generating great results for companies across a variety of industries.

Can you share with our readers the most interesting or amusing story that has occurred to you in your career so far? Can you share the lesson or takeaway that you took out of that story?

When I joined vCita in May 2011, business growth was exclusively product-led. I hired the company’s first head of sales, and we started calling some users of our platform. I recall one funny moment, when our head of sales held the phone and asked me to join a call with a prospect. He needed technical answers from R&D, and I was the closest thing to a developer he could find (make no mistake — I was the CMO). I introduced myself as Ran from Engineering, and we were able to close one of our first deals ever.

One thing I do to this day — whether as VP Marketing in a company with 100+ sales reps, or at my own startup — is to join in on calls with prospects. I make a point to sit with AEs and SDRs and hear their pitch, witness buyer objections, and try to figure out first-hand what’s going to move the needle for them.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

I’m grateful to many people, managers, mentors, investors, and — most important — the people who worked for me. I can honestly say that I have gained insight from each and every one of them.

Particularly, I owe my career shift — from a software engineer to product management and marketing — to Amir Orad, the current CEO of Sisense. 20+ years ago he was one of my first managers. He believed in my potential and later recruited me to become the product manager of a completely new product at another company. I had zero product or marketing experience, yet he hired me and surrounded me with some amazing mentors in sales, marketing and product management.

For the benefit of our readers, can you tell us a bit why you are an authority on the topic of sales?

Throughout my career I’ve seen B2B sales from all different perspectives — as a product manager addressing customers and sales teams requests, as a marketing leader ensuring demand and “air coverage” to our frontline sales teams, and as an executive who managed sales and sales development leaders. This wide variety of experiences, makes it easier for me to understand what works, and what doesn’t work, when it comes to sales.

Ok. Thanks for all that. Let’s now jump to the main core of our interview. As you know, nearly any business a person will enter will involve some form of sales. At the same time, most people have never received any formal education about how to be effective at selling. Why do you think our education system teaches nearly every other arcane subject, but sales, one of the most useful and versatile topics, is totally ignored?

While Sales 101 may not appear on the syllabus per se, I think it’s a bit of stretch to say that it’s totally ignored. Selling is integral to a wide variety of business subjects and can be learned both inside and outside the classroom. Debate is all about “selling” your argument or point of view to a target audience, and is being taught at a very young age. Another everyday example of a sales skill is successfully navigating a job interview. Some of these skills are being taught as “enrichment” workshops, other sales skills such as negotiation are being offered as courses.

In recent years, we’ve seen the specialization of sales training and education into specific aspects of sales, e.g., courses for Sales Development Reps (SDRs) and incubators with certifications.

This discussion, entitled, “How To Be Great At Sales Without Seeming Salesy”, is making an assumption that seeming salesy or pushy is something to be avoided. Do you agree with this assumption? Whether yes, or no, can you articulate why you feel the way you do?

There’s nothing wrong with being passionate about what you sell — in fact, the message your sales team should be conveying is that your product will undoubtedly change your prospect’s life for the better. If this is construed as “pushy” or “salesy” — so be it. If your product doesn’t meet your prospect’s needs, say so and then move on.

The seven stages of a sales cycle are usually broken down to versions of Prospecting, Preparation, Approach, Presentation, Handling objections, Closing, and Follow-up. Which stage do you feel that you are best at? What is your unique approach, your “secret sauce”, to that particular skill? Can you explain or give a story?

At RightBound we are dedicated and focused to prospecting and sales development. We’ve probably spoken to thousands of prospects and seen every flavor of prospecting team and process. As sales development becomes more data and analytics-driven, we realized that technological advancements have made SDRs’ lives more difficult rather than making it better. Surveys still show that SDRs spend most of their time on manual research and list building, rather than engaging with prospects and understanding their needs. The secret sauce is leveraging AI and machine learning not only to provide insights and “advise” the SDR, but actually take a lot of the work off their plate.

Lead generation, or prospecting, is one of the basic steps of the sales cycle. Obviously every industry will be different, but can you share some of the fundamental strategies you use to generate good, qualified leads?

RightBound has an unfair advantage. We use our own autonomous platform for B2B sales. I like to explain this difference using an analogy from the automotive industry. While other prospecting tools in this space are like navigation systems to help aid the driver, RightBound is like an autonomous vehicle.

The RightBound platform searches across dozens of data sources to find and target new prospects, and uses AI to continually optimize your playbook per target individual. This results in a huge time savings for the sales team, and many more accurate, verified and enriched leads.

In my experience, I think the final stages of Handling Objections, Closing, and Follow-up, are the most difficult parts for many people. Why do you think ‘Handling Objections’ is so hard for people? What would you recommend for one to do, to be better at ‘Handling Objections’?

In general, people tend to try to avoid conflict wherever possible and handling objections is exactly that. You’re basically telling someone that their opinion is wrong, and this can lead to an uncomfortable conversation. When an objection is raised, you need to make a split-second decision on how you’re going to act — acknowledge the objection and explain how it can be resolved or dispute it. The key is to be decisive.

There are many different tactics for overcoming buyer objections. If price is an obstacle, demonstrate your product’s ROI against alternatives. If the objection relates to a feature, try to shift the focus from the feature to the need and how to solve it. Regarding competition, do your homework and point out your differentiators.

‘Closing’ is of course the proverbial Holy Grail. Can you suggest 5 things one can do to successfully close a sale without being perceived as pushy? If you can, please share a story or example, ideally from your experience, for each.

Based on my experience, closing a sale when the buyer still has reservations about “fit” is all about minimizing risk for the buyer. Here are five techniques that can help:

  1. Provide customer references and facilitate a customer call or visit
  2. Defuse the “not a fit” argument by showing how you address a real need that emerged during the sales negotiation
  3. Set mutually agreed KPIs and offer money back if they’re not reached
  4. Offer a free trial with no obligation
  5. Propose a PoC on an actual use case

And if these don’t work — you can always resort to reverse psychology and tell them that they aren’t a fit for your product…

Finally, what are your thoughts about ‘Follow up’? Many businesses get leads who might be interested but things never seem to close. What are some good tips for a business leader to successfully follow up and bring things to a conclusion, without appearing overly pushy or overeager?

This is a very sensitive issue. Based on my experience, the best tip is not to follow-up on the same topic over and over again. Like you said, no one likes to be nagged, and aggressive follow-up in many cases is counter-productive. Instead, find ways to start a completely new conversation. Build a constructive relationship with the prospect/lead regardless of whether you close the sale. For example, get in touch if you see a relevant industry article they might be interested in reading, or reach out to congratulate them if you see their company has significant news. Make sure not to bring back the “sell” into the new conversation.

As you know there are so many modes of communication today. For example, In-person, phone calls, video calls, emails, and text messages. In your opinion, which of these communication methods should be avoided when attempting to close a sale or follow up? Which are the best ones? Can you explain or give a story?

Selecting the right channel depends on the stage of the sales and the persona you’re targeting. Each target prospect is unique and the challenge here is to adjust your channels, cadence and message based on the prospect’s behavior over time. For example, with respect to timing, a text message would probably be a disaster early on, but great when you’ve already had ten calls with your prospect.

The channels used need to be fine-tuned and adjusted to fit each individual prospect. There are no hard “no’s” that apply to all situations. A great example is the shift to remote work over the past 18 months. Buyer prospects who used to be available in person or by office (landline) phone during business hours are now working from home and need to be contacted by other channels. Flexibility and the ability to adjust on the fly are essential today more than ever.

How can our readers follow you online?



Thank you for the interview. We wish you only continued success!



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