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Always Wanted to Have a Sneak Peek into Sales of Most Successful Digital Companies? Here's What 6 Salespeople Say about Their Work for Leading Tech Giants

You always wanted to know how is it to work for a company that has a killer sales process and almost consistently outperforms? What makes these organizations different from others and what’s the approach of their salespeople – both reps and managers? Do they face the same challenges and struggle with the same problems?

Paulina Golab

We wondered how many similarities and differences we can find to answer the burning questions related to the best sales tips & techniques, pain points, challenges, and much more.

Not to mention, we wanted to feed our curiosity and discover if the opinions of experienced salespeople differ from those expressed by their peers who are starting out in their sales careers. 

What do they think about their job at the very beginning of their career and how it evolves when they gain more experience? Do they have any inside sales tips, techniques they swear by? Do they use any tools they can’t live without?

We reached out to salespeople working for companies known for their successful sales teams, like HubSpot, Amazon, Oracle, IBM, Sprout Social, and LinkedIn and asked them a bunch of career-related questions. 

Let’s dive in and learn more about their sales secret sauce. 

Why inside sales? What’s most appealing about this career path? 

Many people have negative feelings and thoughts when it comes to sales and sales-related jobs. 

They perceive salespeople as pushy, intrusive, or simply arrogant. 

However, many bright individuals start their career in sales, ignoring negative opinions about this profession.

Raleigh Dugal, Sales Manager at HubSpot, with almost nine years of experience in inside sales, chirps: „I completely fell into sales. After graduate school, I spent two years establishing my writing career and took a job at a startup to build a little extra cash. I just fell in love with the simplicity of understanding success – you’re hitting your number, or your not. I think I’ve learned since then that it’s much more complex than that, but it’s what initially drew me.”

Cillian O Grady, Head of Sales at Sprout Social, with over 25 years in sales (10 years at Oracle), took an example from his dad: „I chose a career in sales because my dad was in sales. Sales management and the variety of work and the people you meet appealed to me. After so many years in sales, I have to admit it was a good decision.”

Neal Schrepfer, an experienced professional  (over 17 years in the business) working as a Sales Manager for Amazon, gave us two reasons: „I had a business mentor that recruited me and saw my potential, and when I saw the financial opportunity, it seemed an easy choice to follow.” 

„Once I was in the inside sales roles, each became more and more challenging. I came to realize that this is a profession; that if followed honestly, will always offer something new and that variety and challenge are important to me in my professional life.”

Ibrohim Johari, IBM, over three years with sales-related positions, admits: „I didn’t particularly choose it, but there was an opportunity, and I wanted to try it out. I’ve never considered sales previously. But here I am, so far, so good.”

Shreya Jain, who joined LinkedIn 3.5 years ago got that feeling of a „click” with inside sales: „I joined the company in the operations team (working on the backend with sales). From day one I realized I have to be in sales because I enjoy building relationships, I thrive when I am challenged and wanted to get that kick of closing a deal and bringing that impact to my organization.” 

Adriana Alvardo, almost two years with Oracle as a little girl dreamed of many professions, but followed her natural abilities: „There was always something that I was passionate about, dealing with people. Even as a child, when I started talking with someone, I began to realize that everything flowed naturally, I could see that my joy was contagious.” 

Biggest pain points in your daily work with inside sales

Raleigh states that many little problems popping up every day that seems urgent are the biggest challenges. Why? „They seem urgent at the moment and ultimately pull you away from the bigger picture. The problem is that in sales, the stakes for ignoring the bigger picture can be much higher.”

Cillian O Grady sees the lack of predictability of results as his most prominent pain point:” As a Sales leader, my biggest pain point is getting a whole team to reach their targets on a consistent and predictable basis. With a wave of consensus-based decision making spreading across organizations, it is becoming increasingly more difficult to identify the full decision-making unit and to understand where the influence lies.”

Surprisingly, Neal Schrepfer sees monotony as one of his biggest problems: „As someone who chose sales, one of the perks of the job is the variety of interactions, and the rapid rate of change is important. Anything repetitive or tedious, or removes the creativity of a salesperson from their day, limits the possibility of that person being successful.”

Operational and administrative work is the most significant pain point for Shreya Jain: „I would like to spend more time in front of my clients/prospects rather than a desktop.”

Adriana Alvardo doesn’t see any particular pain points in her work, but if asked to name one, she replies: „A client who is not happy with the product I offered them and when they have a problem that needs to be solved immediately, and they reach out to me. That could be perceived as my biggest pain point.”

Challenges in the next quarter – big or small


Being a manager, Raleigh has to lead his army of sales reps and their challenges are his challenges: „Our team has changed a bit of our go to market strategy, and our sales reps are always at the forefront of executing that change in customer-facing roles, so that continues to evolve and iterate as we figure it out together.”

Neal is also gearing up to face challenges related to managing his team: „Hiring. Finding qualified inside sales reps who have the right experience for each position is hard. Many sales reps have done various types of sales (inside sales/ outside sales/ phone only/ in-person presentations/ retail/ B2B). Not all of the skills you are happy within one translate to another type. The right fit for the right role is difficult.”

We’ve got implementing new strategies, hiring, so we’re just missing training. 

And here it is, Cillian’s challenge: „I currently lead a team with a lot of new members, and the biggest challenge is to get them to ramp to full productivity as quickly as possible.”

For Shreya and Adriana, the most significant challenges include truly challenging quota and dealing with many everyday tasks.

ALSO READ – Our Sales Team Converts A Prospect’s 'No’ To 'Yes’ With These 12 Techniques (And You Can Too)

Characteristics of a great salesperson – share your secret with us

Raleigh sees resilience as the most important characteristic: „A substantial percentage of the work you do will go unrewarded, and you’ll need the remainder to be brilliant enough to deliver 100% of your quota.”

Neal points out selling with integrity: „If you are selling simply to get someone to buy, you are playing a short game, and you will lose.”

Cillian gives similar things like the two above mentioned sales professionals: resilience and authenticity. He also adds personal drive, good organization, accountability, and above all: „positive attitude is probably the most important trait a salesperson needs to have.” 

Ibrohim Johari brings up perseverance and grit as the two most essential characteristics.

Shreya mentions resilience as her more experienced colleagues. She also lists empathy and laser focus.

Adriana perceives patience as the most important characteristic: „All lies in wanting to convince the client not by force, but by having a well-grounded plan, having great knowledge of your product and being an expert in it.” 

Inside sales techniques that ensure you win those deals

Raleigh Dugal from HubSpot recommends a book which may be a source of useful inside sales techniques: „The Challenger Sale is by far the most effective book I’ve read. Some reps confuse „challenging” with being pushy or closing hard, but it couldn’t be further from the truth. If in your time together, you can help someone gain a new perspective on a problem they have been frustrated with, that value will carry through the rest of the process.” 

Amazonian Neal Schrepfer sees education as the most potent inside sales technique: „The more I can teach a prospect about a service/product and its benefits to them, the easier the task is to close the sale. It is also educating me about the prospect and knowing if they are a good fit.”

Cillian O Grady, Sprout Social and Oracle veteran: „I have been a big fan of the inside sales technique called Sandler Selling for many years. I like it because it is authentic and not manipulative. There are two Sandler techniques which I think are particularly effective when exercised well.”

„The first one is the upfront contract – which helps the salesperson and the customer navigate jointly through the process, without surprises. The second inside sales technique is called the Pain Funnel – which is a very effective questioning process which uncovers the real impact of a challenge a customer has both from a business and personal perspective. It helps both the customer and salesperson understand the value the solution the salesperson is presenting will have.”

Shreya Jain, LinkedIn, and Adriana Alvardo, Oracle, don’t name any particular inside sales technique. Shreya says, „picking up the phone,” and Adriana suggests listening to the customer and giving them what they need.  

What’s your “secret” weapon – inside sales calls, emails, or face to face meetings? 

Raleigh shares his experience: „99% of our selling is done via inside sales calls and video conferences. I do find video conferences distracting until I started hiding the self-video so I couldn’t see the expressions I was making as a sold. I’m not sure you can accomplish much via email other than getting meetings booked or following up on questions.” 

„I do enjoy the social capital that face to face meetings build, but as sales continue to evolve, I think more companies will evaluate when/where they are effective.” 

Neal prefers selling face to face instead of making inside sales calls: „Body language is everything. It is hard to soft qualify/disqualify a prospect when you cannot see their facial expressions and body language. It is not impossible over the phone, but it is harder.”

Cillian states, „I’ve always enjoyed face to face selling as you get a real sense of the company and people you are meeting. However, overall, I have found inside sales calls to be the most productive and effective. With the advancement of Web Technologies showcasing a product is as easy remotely as it is face to face (arguably even easier as you are in an environment that you are familiar with and can control as opposed to in a customer’s office where maybe you can’t connect to the Internet or get your laptop to connect to a screen in their office). As decision making units are often geographically spread it can become harder and harder to find a suitable time for a face to face meeting and you certainly can’t fit in as many as you would do via phone. 

Email has a role in the Sales process in terms of sharing information, contracts, etc. but I think Salespeople who over-rely on it as the primary method of selling tend not to be in as much control as others. I guess the right Sales approach also depends on what you are selling. If you are selling something tangible like a Car, Machine, Food, etc. Face to face is probably more effective as the client can touch and feel the product.”

Ibrohim Johari values a mixture of all: inside sales calls, emails, and face to face meetings if possible. He perceives the face to face meetings as an excellent option for longer sales cycles.

Shreya and Adriana prefer to sell while being face to face with a prospect, because of the power of gestures, but they also value inside sales calls.

ALSO READ – Discounts During Inside Sales Calls – How To Give Them Without Losing Dignity?

Inside sales tools top-notch salespeople use

Raleigh recommends Vidyard as a great inside sales tool: „It allows you to send short videos and screen shares to prospects via email. It’s a great way of easily and quickly customizing your outreach or setting yourself apart from the competition.” 

Neal is not that much into fancy inside sales tools, he states: „Using your ears. Your prospect will tell you; directly or indirectly, whether or not you are a value to them. The less you listen, the less you win.” 

Cillian, says that many inside sales tools can make salespeople more productive and effective, especially in phone-based selling: auto dialers, call recording and analysis software, contract signing tools, screen sharing/video conferencing technologies, email tracking software, and business insight tools are in his opinion must-haves.

Ibrohim Johari names a good, reliable CRM and LinkedIn sales tools as his best-performing inside sales tools. Shreya also recommends LinkedIn tools. 

Adriana also uses LinkedIn a lot, but, being based in Mexico, WhatsApp is one of her most important inside sales tools. She adds: „In short, the tools are effective as long as you know how to use and utilize them properly.”

Talking to a prospect? – how to do it (not only right but) best

Raleigh says: „Paying close attention.” straight away. He continues: „Too many reps get distracted, they will check Slacks or emails while on an inside sales call with a prospect, afraid they’ll miss something important. If you’ve chosen to spend time with a person in a business capacity, there’s nothing more important than staying present with that person for the duration of the meeting. „

Cillian gives us almost the same idea as Raleigh, which is: „To listen to the prospect and to spend the time trying to understand their situation and what they are trying to achieve.”

Neal sees „the awareness that you need to be more of a value to a prospect than they are to you” as the most important. 

Shreya thinks decent research before outreach is the most important in inside sales.

Adriana thinks being sincere is very important: „The customer knows when you’re cheating. In my sales career, I have learned that talking to the customer truthfully about what your product does or doesn’t can make a difference and save you many post-sale headaches”.

Any piece of advice to your younger “sales” self?

Raleigh and Cillian both agree they would advise their younger „sales” selves never to stop learning, developing their skills, and getting better. Raleigh underlines: „Your product will change; the market will change; YOU will change. If you sleep on change, nobody else is going to wake you up.”

Neal adds: „I would tell a younger me that integrity is everything. Those people who are taking shortcuts and doing unscrupulous things around you are not winning the long term game like you will if you keep to your standards in dealing with your customers.” 


There you have it. The secret sauce of salespeople from a few of the top performing companies globally

While there are many similarities, what we have learned is that there seems to be a contrast between salespeople in terms of their approach, both the experienced and the young ones included.

Also, professionals with +15 years spent in business may have different opinions on the same topics.

It boils down to this fact – getting your basics right and then adapting your sales processes depending on the industry/product you’re pitching.

We hope you treat this a guide and understand the processes that companies like HubSpot, Amazon, Oracle, LinkedIn, Sprout Social adopt.

What’s your biggest takeaway from all of these sales ideas and approaches? Do you also employ the same processes? 

We’re curious. Let us know in the comments below. 

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