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“Keep that optimistic and youthful candor everyone is born with.” With Mitch Russo & Garrett Schwartz

I think there is nothing more important than keeping that optimistic and youthful candor everyone is born with. For me, nature is something that allows me to do that. Exploring new places while backpacking the great outdoors with friends, snowboarding, mountain biking, picnics in the park, you name it. No matter what your background is […]

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I think there is nothing more important than keeping that optimistic and youthful candor everyone is born with. For me, nature is something that allows me to do that. Exploring new places while backpacking the great outdoors with friends, snowboarding, mountain biking, picnics in the park, you name it. No matter what your background is or where you come from, I think everyone can find something beautiful in nature; and preserving that beauty, for generations to come, is important to all forms of life. I’m a big advocate for sustainability, preservation and taking care of the home that was given to us by mother earth.


I had the pleasure of interviewing Garrett Schwartz. Garrett Schwartz is a Product Marketing Manager for Adobe Document Cloud. He has sales experience in a range of high-technology markets — from enterprise storage, to virtual machines and hypervisors, to thin clients — and now Adobe Sign. Garrett is passionate about bringing Adobe Sign’s transformational power of e-signatures to his customers, focusing on the value that document processes and solutions can bring to large and small businesses alike.


Thank you for joining us GarrettCan you tell us the “backstory” about what brought you to this career path?

Sure, I’d love to. Like many college graduates, I didn’t know what I wanted to do after completing my program. I landed in sales while I took some time to decide. These were inside sales, cold calling, tip-of-the spear type of jobs. As I spent some time doing that, I started seeing the value in it. So, I put my head down, learned the technology and progressed forward to develop a decent sales career. Well, the investment paid off. A Product Marketing Specialist role for Adobe’s Document Cloud business presented itself and I immediately jumped on it, as that is not something that you shy away from. It was time to put my head down again and implement what I had learned since my post-college days. Three years later, I am the Enterprise Lead for Sales Enablement and Evangelism for Adobe Document Cloud.

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?

This one time… at band camp…just kidding. Hey, remember, personality is a big part of sales. Five months into my job at Adobe, still cold calling prospects – I found myself on the main stage of Adobe’s sales conference in Las Vegas to present a customer value presentation in front of our entire Digital Media Sales organization, including two c-level executives, several other leadership members and countless peers; roughly 600 employees. Also, the presentation was a competition between 50 teams for best presentation. I was terrified; borderline blacked out at the end. But, I ended up winning the ‘Crowd’s Choice’ and ‘Judge’s Choice’ awards for best presentation. Gold medal in both!

Did I jump at the opportunity? Absolutely not! I actually sat silent and let my team voluntell me that I was the one who had to present.

Did I think – “Don’t do this, Garrett!”? You bet I did.

Did I follow through? Yes!

And I am glad I did. That ended up to be the most pivotal moment in my career. Do not be afraid to be afraid. It is natural. Everyone gets nervous but if you don’t get out of your comfort zone you never grow. It is also very important, once you’ve committed, to go ALL IN. Bring the energy, bring a lot of confidence, but not arrogance. Even if it is not the greatest presentation, sell it! Your peers, clients, or prospects will respect you for giving it your all. The effort does not go unnoticed.

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

I am, yes! At the moment, I am working on several projects supporting enterprises in adjusting to today’s environment and adapting to a remote workforce. We want to be a partner to them so that they may empower the newly growing generation of the modern day worker. I think it is going to be the next “Great Awakening,” and it is very exciting.

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?

There are many people who have made lasting impressions on me throughout the years, and at the top of the list is my current manager, Lisa Croft. Lisa is our amazing Director of Product Marketing here at Adobe, but her professional history is just as impressive – Coder, Technical Architect, Solutions Consultant, and more. She has really been there for me every step of the way. I’m one of those people that needs to understand the why and the how of things we are doing to really understand where we are going. She knows how to tell that story. Lisa is a wealth of knowledge, she is direct and clear, and an impactful mentor.

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

I haven’t just talked the sales talk; I have walked the sales walk. I have learned something from every one of the best sales professionals that have come through Adobe and continue to work very closely with our top sales leaders – continuing to work towards regularly understanding their needs, but most importantly, how to execute against them. It is a very rare thing to be in a position where you get to see both sides of the Marketing business and Sales coin so often.

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?

Both. There are degrees of sales approach and those degrees are appropriate at various times, you just have to match your degree with the customer’s behavior. I sometimes work at farmers markets selling peaches in my spare time – my girlfriend’s father is a peach farmer. The talk track that I am going to have with the customers at the market is completely different from the tone and the talk track that I have with a CIO at a Fortune 500 company – but they are both valid. The #1 rule is “Tell a good story.” But make sure it is an appropriate story for the mood and temperature of the situation. Don’t be too pushy and do not force anyone to see your vision as it is a waste of time.

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?

Preparation, Approach, and Presentation all live in my sales sweet spot. For example, Presentation. I pride myself at being able to tell a great story that my clients can get on board with. From there, everything else will work itself out. It turns a sales pitch into a conversation, which leads into clients asking “Ok, so what do we have to do to get this done?” This is exactly what all sales rep want to hear.

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?

A basic strategy is knowing which personas to reach out to for specific products. Once that is done, and you get the meeting, come to the table with something that is important to them.

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’?

I agree. Initial objections are often seen as the end of the attempt, when they should really be seen as a part of negotiations.

For example, when dealing with a customer that pins you against your competitor; you have to be able to know you competitor’s solutions better than their own reps do so that you can use that to your advantage to counter offer. The most dangerous sales reps that I have worked with are borderline experts on the general market. It doesn’t take very much time to do a couple of google searches on the market presence of the solution you are selling and who the top dogs are in that field. Note those competitors and start doing your research.

‘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.

  1. Identifying the person that can VETO a deal. In my opinion, this is the most important piece of advice I can give. Everyone always asks who can approve who can approve who’s the final decision maker… it’s really the people that can veto a deal that you have to worry about. Make sure that their needs and requirements are addressed early and often.
  2. Be very direct. This does not mean pushy. It’s more about being clear. This applies to your overall communication and approach. Take questions, for example. Be direct in your questioning and take nothing less than the answers you need to do your job. Sales reps are consultants of the modern business environment, we need to start acting like it.
  3. Time Management. Choose how to spend your time wisely.
  4. Be a good and communicative partner. Nobody wakes up in the morning and wants to fail their prospects. Everyone wants to be successful in what they are doing for their potential or existing customers. It is your job as a sales rep to make the customer feel comfortable in deciding to go with your solution. Is it support? Is it the ease of migration? Is it going to help their bottom line? Make sure that you have those conversations throughout the sales cycle.
  5. Get the commitment as part of the close. Get your customers to commit, whether it is in writing or verbal. If you get someone to commit, they are 70 percent more likely to follow through with your ask.

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?

Oh, follow ups are a must! But, there are ways to do it. Depending on how you acquired the leads; hot or otherwise, I would space out follow up pulse points to make them seem more casual and supportive. Think of it as a “I’m here if you need me,” type of message to begin with and then continue with more collateral on the pain point that your solution is solving and close with providing data or anecdotes on what it is doing in the market.

One more quick tip is to have sales generation reach out so it is not such a cold call.

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?

Personally, I’m not a fan of text, SMS, or messenger conversations for external or internal stakeholders, unless it is more urgent and requires a quick response. My recommendation is to avoid that style. My favorite mode of communication is always in-person meetings or video conferencing calls if possible. That’s how you really start to build a genuine relationship with your clients, team mates, or prospects.

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. 😊

This is such a great question, and one that should be asked to more professionals. I think there is nothing more important than keeping that optimistic and youthful candor everyone is born with. For me, nature is something that allows me to do that. Exploring new places while backpacking the great outdoors with friends, snowboarding, mountain biking, picnics in the park, you name it. No matter what your background is or where you come from, I think everyone can find something beautiful in nature; and preserving that beauty, for generations to come, is important to all forms of life. I’m a big advocate for sustainability, preservation and taking care of the home that was given to us by mother earth. ☺

How can our readers follow you online?

Most active on Linkedin @garrettschwartz

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