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“Be patient.” With Mitch Russo & Philipp Reichardt

don’t be the sneaky used car salesman of your industry. When salespeople demonstrate that they only want to make a quick sale, customers won’t have any interest in engaging. Those reps who have their customer’s best interest at heart by focusing their approach on providing value, however, can create urgency without imposing their own agenda. […]

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don’t be the sneaky used car salesman of your industry. When salespeople demonstrate that they only want to make a quick sale, customers won’t have any interest in engaging. Those reps who have their customer’s best interest at heart by focusing their approach on providing value, however, can create urgency without imposing their own agenda.


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 Philipp Reichardt. Philipp runs sales for North and South America at 2Checkout, a global payments and eCommerce company, where he oversees a team of SDRs, mid-market and enterprise reps. He has over 15 years of experience in leading global sales roles and successfully sold into some of the world’s largest Fortune 500s, as well as cutting edge technology companies. Philipp is a strong believer in the need for sales reps to continuously learn and improve their skills and does weekly coaching sessions with all his direct reports and expects them to do the same with theirs.


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?

Very early on in my career I was fortunate to be accepted for an internship with the eCommerce department at Dell Computers, in Germany. At that time, Dell was a big deal and the first company to sell computers directly to consumers online. It was absolutely fascinating to be part of that team and a great way to start my career. My job at Dell was all about finding new partners for online promotions, helping pitch online product placements and fighting for website real estate internally with the B2B team. I realized very quickly that my eCommerce job was actually a sales job and I really enjoyed that aspect of it. After Dell, I had two runs at starting my own company: a managed IT service provider and a community-based how-to website. Again, what made those endeavors successful was the fact that we managed to sell our products to new customers and it was exactly that part of running the companies that I enjoyed the most. I was then given the opportunity to help grow the North American business for a German software company and ultimately ended up in the US, where I really hit the accelerator on my sales career. I worked for both, smaller startups and publicly listed companies until I ended up at my current job as VP of Sales at 2Checkout, a fast-growing payments and eCommerce provider.

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

At one point, I was in charge of Business Development and Sales for a consumer privacy protection software. We were working on getting listed with all the big eTailers at the time (think Buy.com, PCMall, Amazon) and tried to convince TigerDirect to carry our products, too. When we finally got the meeting, we flew down to Miami, and struck a deal to get our products into their online catalogue for 30 days, in an effort to “prove ourselves”. At the time, a lot of people still called in to place their online orders, so TigerDirect had an army of sales reps doing nothing but taking orders every day. One way of doing well as a software company was to make sure every one of those reps knew about your product and offered it as an upsell to people buying laptops or other products. Consequently, we trained the reps, distributed flyers on how to sell our products and even offered bonuses for every license they sold. However, despite our best efforts we had a horrible launch, to the point of getting threatened to see our products pulled sooner than 30 days if things didn’t pick up. We were staying in South Beach that night and while we were strategizing on what we could do to get TigerDirect’s sales rep’s attention, a guy walks by with a baby tiger on a leash. It was Florida after all. We put two and two together and the next day, a baby tiger showed up at TigerDirect’s parking lot, offering free pictures to be taken with our company’s logo in the background. Everybody loved it and was happily made aware of our products. Sales went up after that, and TigerDirect became one of our best channels at the time. There was that detail of the strongly worded letter from a certain legal department asking us to never show up with a tiger again, but it all worked out and everybody was happy at the end.

Are you working on any exciting new projects now? How do you think that will help people?

Certainly one of the perks of working at 2Checkout is that you get to see a lot of new projects by companies that are changing the way they do business and serve their customers. Even before COVID-19, there was a strong trend for companies to build deeper relationships with their customers online and now this trend has accelerated dramatically. We are working on very interesting ventures with some of the world’s largest corporations. Many of these projects will have a lasting impact on how we as consumers will interact with these companies. Be it enabling your printer to automatically order ink refills or have your car pay for parking by itself, there are some interesting use cases our customers are solving. We also see a lot of new marketing or sales tools and a plethora of subscription use cases taking off. One of my favorite examples right now is an app that Xerox just launched, which taps into their massive global supply chain and customer network, allowing them to help dispatch health care workers fighting the COVID-19 pandemic. We’ve helped them set up their global online distribution channel. To me, this is such an inspiring story of how one can use technology and access to resources to create a solution that can help and have a lasting impact on millions of people.

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?

Honestly, there were so many people in my life who really propelled me forward in my career, pushed me to get better, and trusted me with more responsibilities than I deserved, that naming just one of them would do injustice to the others. I think a common theme for me is that I get along well with my superiors and develop great relationships with the people I work with. Most people can see that your heart is in what you do and that you’re open to feedback. This attitude along with an insatiable appetite to keep learning led to many coaching and mentor relationships along the years, all of which contributed to getting me where I am today. Many of the people I worked for remain friends and the time spent with all of them was highly appreciated.

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

As I shared previously, I worked in sales for my entire career. Be it at large Fortune 100s closing multi-million-dollar contracts or small startups celebrating another 1,000 dollars in MRR, I have seen and lived through how important and transformational it is for an organization to excel in sales. I also know that this is a hard career to follow. Whether cold calling for hours and dealing with countless rejections or spending weeks and sometimes months on an account only to not get the deal; I’ve built my career on learning how to overcome those challenges. As a manager of sales development, mid-market and enterprise reps, I’ve also learned how to build a well-oiled sales machine, establish processes and employ the right technology stack to make a team more efficient. Finally, as an entrepreneur-turned-sales-manager, I serve as an advisor to multiple startups in the Bay Area where I helped optimize and coach various sales teams. As an early angel investor in People.ai, for example, I helped build the company’s first data models and sales coaching tools, now used by sales teams at Lyft, Zoom, and Zendesk.

Let’s shift a bit to what is happening today in the broader world. Many people have become anxious from the dramatic jolts of the news cycle. The fears related to the COVID-19 pandemic have understandably heightened a sense of uncertainty and loneliness. From your experience, what are a few ideas that we can use to effectively offer support to our families and loved ones who are feeling anxious? Can you explain?

Sadly, just two weeks ago I have lost a dear friend from high school. He was the best man at my wedding and someone I cherished a lot; however, it had been a while since we last spoke. This, along with the forced separation from our friends and loved ones during the various lockdowns around the world, really reminded me how important it is to stay in touch with the people we care about. My number one piece of advice on this topic is to maintain communication, check in on people and listen to what they have to say, how they are coping with the current situation and what they may need to get through this. Take advantage of the current lack of distractions to (re)connect with the people you care about. You reaching out might just make their day! So many times, it’s the fact that someone listens to us or provides small words of encouragement that make a big difference in our lives. Also, don’t be afraid to share how you are doing either: many times opening up first will lead others to trust you and open up, as well.

It’s also good to stay busy, volunteer, help others, pick up a project and focus on positive things in your life. Ask people to help you if they are not busy at the moment. Show others that they matter, give them a chance to be part of something and create a sense of accomplishment.

Finally, don’t forget that we humans are a resilient bunch and like so many other challenges we faced, this too will pass, jobs will be back, and new opportunities will be created. Times of crisis like this one have historically been great sources of innovation and transformation. I’m certain we will see similar long-term positive effects from this, as well.

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?

Don’t get me started about the education system… We could have a whole separate interview on all the things we do wrong when it comes to teaching our kids how to be successful in today’s world. Most schools unfortunately still focus too much on syllabus rather than creative learning. The problem is that just like many other skills needed to thrive in our economy, sales in itself is hard to teach in an academic setting without any real-life context to apply what you learned. Yes, sales processes are important to know but they won’t mean much to students unless they can apply them. Schools should therefore spend much more time on fostering an environment of “creative creating” with real-world exposure that focuses on problem-solving outside of the textbook. A successful salesperson is a problem-solver who can quickly adapt to a new situation, is disciplined, humble and empathetic to the people he or she interacts with. Few of those skills are taught by the current education system.

This discussion, entitled, “How To Be Great At Sales Without Seeming Salesey”, 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?

I think it all depends on the context. Being assertive and insistent in a large deal that is about to close is definitely OK, expected even, while being salesey and pushy on your first date is maybe not such a good idea. All joking aside, don’t be the sneaky used car salesman of your industry. When salespeople demonstrate that they only want to make a quick sale, customers won’t have any interest in engaging. Those reps who have their customer’s best interest at heart by focusing their approach on providing value, however, can create urgency without imposing their own agenda. The perception of salespeople being too salesey generally stems from an approach that is focused on “what’s in it for me” as opposed to “what’s in it for my customer”. A good sales professional is very aware of the difference and earns the trust of their client by providing value and thus creating a win-win situation.

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?

Prospecting is definitely the part of the sales process I like the most. I enjoy working with and meeting new people and can be extremely creative in finding ways to approach them. Seeing how new relationships can turn into large projects with lots of people involved is absolutely fascinating for me and a big motivation during the prospecting phase.

When it comes to my secret sauce, one of the things that works well for me is to take a moment and find something I can admire in the person I’m talking to. I don’t have to like or even know them; there is always something I can come up with that is admirable. I learned that by focusing on the positive in people, we subconsciously start smiling and look at them differently. This will create a sense of respect that’s very different from just trying to be nice or polite.

Secondly, I try to be true to who I am, no matter the situation. We need strong anchors to make sure we don’t get washed away. This is a quality that will ultimately earn you more respect than just pleasing everybody you meet. I think that it’s important to be known for and have a conviction that we can stick to. Rather than agreeing with everything a prospect says or wants, challenging them and respectfully disagreeing will many times lead to much better results as long as it’s part of a consistent story and conviction. This is also true for other stages of the sales process.

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?

Knowing who your customers are and where to find them is obviously the first question to answer. What problem is your solution solving and who can benefit from that the most? Do you have existing customers who you can learn from and who might even be willing to refer you? Are there tradeshows that are worth attending? At 2Checkout, we are lucky to work with a great marketing team that creates inbound leads through online marketing and social media campaigns. There are also tools that can help you discover prospects who use a certain competitor or complementary product. All of those areas are worth evaluating to determine what mix works best for your target audience.

Once you identified the source of accounts and hopefully a list of names to go after, it’s all about getting their attention and making sure they are an actual fit for your solution. When prospecting accounts you may not always have the luxury of contacting everybody with a highly customized message or phone call. While you should always strive for that or have at least a list of top accounts that you target individually, there are a few general pointers that will lead to more success in lead generation:

  • Be relevant: Focus on the problem you can solve and how that is applicable to your target audience. Don’t reach out with overly generic messages.
  • Be creative: Try contacting multiple people in the organization you are targeting, test different messaging and mix up your channels of communication. Email, Phone, Linkedin, or text work best when used together.
  • Be memorable: Create your unique style of engaging, be friendly, funny and familiar.
  • Be patient: Don’t give up just because you don’t get a response right away. Most prospects need over 20 touches before they respond.
  • Be respectful. Learn the difference between being assertive and aggressive. Stand up for what you know can add value for your prospects but respect their wishes to not be bothered at the moment.
  • Play the numbers game: Don’t forget that for every yes you get about 99 nos.

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’?

Nobody likes rejection; especially by strangers and even more so when our livelihood depends on overcoming them. What salespeople need to learn is that every rejection and objection brings them one step closer to a signed contract.

There are two common mistakes when it comes to objection handling. First, we try to explain our way out of it by providing reasons as to why we are right, and the customer is wrong. That’s the wrong approach and I will explain in a minute why that’s the case. Second, many times reps haven’t done their homework during the sales process and thus are ill equipped to properly tackle objections.

Let’s look at the homework first. Before we can do proper objection handling, we have to truly understand the customer’s current issue, problems or needs. Many sales reps, however, jump straight to objection handling from prospecting without doing a proper discovery session first. A good discovery is crucial to understanding what drives a customer, what they care about and what constitutes success for them and their company. Without that knowledge, your objection handling will be like shooting in the dark.

Once you know what drives your prospects you can be very effective at tackling their objections. Here it is important that instead of convincing people by throwing a bunch of good reasons at them, you help your prospects convince themselves by asking the right questions. For example: rather than telling someone that they will make 8% more profit with your solution, ask them to do the math and get to the conclusion by themselves. After reaching that conclusion continue asking questions to remove further blockers, such as risks, resources needed or other concerns they may have.

Proper research will arm you to find the right questions and guide your client to what you know is ultimately going to benefit them. The result should be that they can’t afford not to work with you.

‘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.

Just like with objection handling, closing is when it will really show if you’ve done your homework during the sales process. Do you have buy in from multiple stakeholders at the company? Do you understand any potential obstacle that could come between you and a signed contract? It’s so tempting to jump straight for the close during the selling process instead of following a process. While this may work in smaller, less complex deals, having that one enthusiastic champion ready to move forward may not be enough to bring the deal home in the enterprise space. You should not trust that one person has the power to get the deal over the finish line and need to make sure you get support from everybody else who has a stake in the decision. So do your homework, follow the sales process and don’t leave any room for surprises.

Another very important tool is a clearly defined close plan that you and your prospect have agreed on early in the process. This plan will lay out what it will take from both sides to get to a signed agreement. Work on this jointly with your prospect and have them agree to the milestones and deliverables with a timeline attached to each one. During the sales process you will then work your way through the plan and have your prospect participate in checking off all the steps you have agreed on. This way, there is a clear deadline and path to get to signature, making it easier for you to hold them accountable to actually move forward.

Finally, don’t be afraid to ask for the close. Hopefully by the time you get to the closing stage, you’ve developed a relationship with your prospect and gained their trust. You’ve shown them the benefits they will reap from your product and they know you and your company will be around to continue to support them going forward. At that point, there is nothing wrong with directly going for the close and asking them to move forward. You can also share how important it is to get a contract signed by a certain time, such as the end of the month or quarter. Most buyers understand the need to get deals booked and are willing to work with you on making it happen.

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?

At this point, you can probably find a theme in my approach … just as with the other steps when it comes to follow up, it’s important to do your homework first, provide value and not just follow up for the sake of following up. Instead, offer something that’ll benefit the recipient. Find information that’s relevant and useful. Maybe an interesting article, a case study of a customer with similar issues or a reference to something they said in an interview, shared on social media, or similar.

Be consistent but don’t spam them. Definitely try multiple channels of engagement and don’t be shy to offer to meet in person when you happen to be in town. Most importantly, keep it friendly, not too formal, even a bit funny when you can so that you stick out from all the other people chasing your contact.

Finally, even if you don’t get an answer or reaction to your follow ups, you should behave as if they were read and received. Don’t re-introduce yourself with every email or sound like you resent them for not responding. They may just be busy, and your product may not be a priority at the moment. If you play your cards right, however, you’ll be the first person they call once there is a need for what you are selling.

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?

Apart from calling someone’s personal home phone (do people still have those?) or reaching out on Facebook/Instagram, there really isn’t any method that is off limits in my opinion. In fact, I’d recommend trying all of them at moderation to see which one your prospect or client is most comfortable with. Especially the less formal ones can be a great way to remind people to answer that long email you sent last week. Additionally, be sure you understand regional differences. WeChat is the way to go in China, Line in Japan and the same is true for WhatsApp in South America or India while Americans still mostly use text message.

A good story about the importance of proper communication channels is from one of the startups I was advising. They spent months dealing with a Chinese prospect via email and phone without getting anywhere. Emails weren’t answered for days, and phone calls were challenging due to the language barrier. Once they finally opened a WeChat account, they were able to communicate more efficiently, understand the customer’s concerns, send pictures and drawings of what was missing and close the deal only a few days later.

Ok, we are nearly done. Here is our final “meaty” question. You are a person of enormous influence. If you could inspire a movement that would bring the most amount of good to the greatest amount of people, what would that be? You never know what your idea can trigger. 🙂

Besides the obvious need of banning stickers on fruits (really, someone needs to stop that!), I’d circle back to the topic of education. Let’s all work together to create a new status quo on how kids around the world are able to learn and grow into the creative critical problem solvers they need to be to succeed. I’m inspired by some of the changes happening currently with so many students learning from home and hope that we can collectively learn from this situation to help children be more autonomous in learning going forward.

How can our readers follow you online?

My Twitter handle is @re_phil, I can be found on LinkedIn at linkedin.com/in/philreich/ and I’m frequently seen on Reddit, as well

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

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