Hiro Rodriguez

by Keith Krach from LOS GATOS, California in United States

Hiro, My Hero

For four years, it has been my pleasure and my privilege to know and to partner with my Chief of Staff, DocuSign Director of Executive Engagement, and personal Hero, Hiro Rodriguez.

130792With my Hero in JapanKeith Krach personal photo 

Hiro, the Beginning of the Journey

My relationship with Hiro began when, as CEO of DocuSign, I started searching for a new Chief of Staff—a sharp young professional I could mentor, and who would be my right hand in all things DocuSign—especially someone with the judgment, finesse and dedication to help manage and expand executive relationships for me and for the company. What I have found in Hiro is so much more. Over the years, Hiro has been an indispensable Chief of Staff, a champion and director of DocuSign executive engagement, a protégé, a mentor, a brother, a family member, and a dear, dear friend.   

Hiro came to our first meeting with impeccable credentials. He had attended the University of San Diego and graduated with a BS in Political Science. He began working right after college and in three short years had became an expert at Salesforce, presenting the full suite of Salesforce products to C-level executives. Hiro was recognized by his peers as an all-star and had caught the eye of my then Chief of Staff, Mike Arrieta. Mike decided early on that Hiro was the right guy to recruit as his replacement.

Hiro, the Chief of Staff

Right from the start, it was clear that Hiro was the perfect man for the job. Hiro immediately saw the strategic value of the DocuSign Advisory Board, and began to forge a wide array of personal relationships and partnerships with business executives and leaders from around the world.

130768Hail to the (new) ChiefKeith Krach personal photo 

Over the years, he has helped grow the DocuSign Advisory Board into a world-class cross-section of leaders that includes government officials, social entrepreneurs, Fortune 500 CEOs, Silicon Valley executives, leaders in higher education, all-star athletes, and influential members of the press—over 200 in all. His efforts have not only resulted in strategic advice from the advisors but also drives significant revenue, brand awareness, and global growth for DocuSign.

A few years ago, Hiro has been an invaluable partner, as we focused on increasing our DocuSign opportunity in Japan. By focusing on trusted relationships, he helped secure and solidify DocuSign’s Japan Advisory Board which consists of some of the most powerful and influential leaders in the country, including the CEO of NTT, Former Chairman of Japan’s Real Estate association, and the Head of Alibaba Japan. Hiro also helped bridge the gap between DocuSign HQ and Japan on many topics. He successfully supported Japan in product development, currency development, marketing initiatives and business development.

Hiro has also rewritten the cookbook when it comes to driving executive engagement for DocuSign’s enterprise sales team. On large deals for DocuSign, Hiro has developed a very effective approach to address opportunities. His deep understanding of how CEOs and leaders think allows him to prepare for meetings with a competitive analysis ready in advance, a brief that goes into detail on exactly what DocuSign use case opportunities we can explore, and how to position DocuSign to be a vital solution to business challenges. After the meeting he prepares and executes an extensive and detailed follow up that positions the account rep the information needed to move the deal forward, gain valuable inside support, and get quickly to close. 

130769Making DocuSign a Huge SuccessKeith Krach personal photo 

He has literally done this 100s of times and on a daily basis. His ability to direct, guide and lead the enterprise VPs in their never-ending quest to identify the next Walmart, New York Life, Cisco and countless others is uncanny. Virtually all of these large deals have all inevitably gone through Hiro. Almost every congratulatory email I receive on our biggest deals will specifically call out Hiro.

Hiro’s work ethic, his organizational skills and his project management skills all come into play to create a winning combination for DocuSign.  This process scales well and Hiro’s value to the company is multiplied many times over because of his ability to set up others for success. He is a “True Multiplier.”

Hiro, the Mentee

From our very first meeting, I knew our relationship wouldn’t stay stuck on a professional level. I saw a spark in Hiro of someone with a thirst for knowledge and a passionate desire to learn and grow on all levels—professional, personal, social, emotional—someone who would be open to genuine connection and mentorship.

130770Getting a Little PersonalKeith Krach personal photo 

And it wasn’t long at all before our relationship deepened to that level. Hiro has courageously shared his hopes and dreams, weaknesses and strengths, and together we’ve mapped pathways for him to grow to his full stature as a leader and have the impact I believe he is destined to have in the world.

Hiro’s executive engagement work with the DocuSign Advisory Board has also given him the opportunity to build an extensive network of mentors—something he’s done with relish. I’m thrilled to see how many connections he’s made with so many mentors who have each enriched his life in so many ways. It takes a rare degree of openness and a true thirst for learning to learn from so many mentors.   

Hiro, the Mentor

With the right people, mentorship becomes a two-way street. And I’m honored to count Hiro as mentor of mine. Hiro is a master at giving me the input I need. Sometimes that means he’s helping me sound like the smartest guy in the room by prepping me like crazy for an important meeting. Other times it’s about helping me to say “no” when I lack the perspective or self control to see my own limits. And sometimes Hiro tactfully steps in to let me know when my ideas are far-fetched. Despite that, he even helps me get some of them across the finish line anyway.

In true Hiro form, he’s a mentor to others as well. Not long ago Hiro was invited to present some of his insights on leadership and mentorship a group of sales interns at DocuSign. In their own words, they said:

  • “He is awesome! It makes sense after hearing him speak how and why he has been so successful in his role at DocuSign.”
  • “He mentioned that he uses a kind of hybrid mentor graph to describe who his mentors are based on the X-axis (characteristics like public speaking, strategic mindedness, etc.) and the Y-axis (people such as Steve Jobs, his father, etc.). I think this is a brilliant way to show why you think of your mentors as mentors.”
  • “I also love what he said about mentees and mentors. Hiro kept saying ‘be a sponge.’ I know Hiro’s messages will really be applicable for me throughout my life.”

130790Sigma ChiPublic domainHiro, my Sigma Chi Brother

Last year we opened another new chapter, when Hiro was officially initiated into the brotherhood of the Sigma Chi fraternity. Hiro’s background and love for leadership is exactly why Sigma Chi created its non-student initiation process when I was Grand Consul 12 years ago.

Hiro exemplifies Sigma Chi values in his work and personal life. He has attended many Sigma Chi events with me and has personally taken time to meet with Sigma Chi Brothers who reach out to me for advice and help in looking for their next career move. 

His loyalty and leadership alone whole-heartedly embody the true values and ideals of the Sigma Chi fraternity. I had the honor of pinning the badge of Sigma Chi on his chest and thought of the words the seven founders used Founders used on June 28, 1855:

“I place this White Cross over my heart, because it appeals both to my intellect and to my affections. I wear it with a deep sense of humility and with a feeling of unworthiness; Believing that the world expects more of me than the world expects of other men, and realizing full well that I never can conquer by a sign, even though it be a cross. But only as the ideals for which this badge stands take possession of my heart and become exemplified in my life, will I ever know the deepest meanings of the White Cross of Sigma Chi.”

Hiro, my Son’s Boss, Mentor, Friend and Brother

130772Carter, Hiro and meKeith Krach personal photo 

I’ll never forget when got the call from my Boilermaker son, Carter. He had just decided that after spending three years as a professional actor, he wanted out. Despite being a paramedic on Grey’s Anatomy, and doing Indie films and a few commercials, Hollywood was not the place for him. I pressed him hard and said are you sure? He said it’s not a team sport in Tinsel Town and he wanted to be part of building something. I said, like what? He told me he wanted to get in the software business but  he didn’t know where to start.  Instantly and instinctively, I blurted out, “You gotta work for Hiro. He can teach you everything you need to know and he would be the best mentor in the world. You guys will end up being brothers.”

Like a flash, I realized the best thing in the world for my son would be to come work for Hiro. As a young man, Hiro could make a connection with Carter that I never could as his dad. And I could think of no one in the world I’d rather have Carter get to know and learn from than Hiro.

In the months that followed, I saw an incredible relationship take root and grow. A relationship that both Carter and I will cherish forever. Hiro became Carter’s boss, mentor, friend, and brother. It was a wonderful gift, for me, as a father, to stand back and watch the two of them build a trusted bond, and to see my son learning lesson after lesson from Hiro about work, life, family, and manhood.  A year later, Carter launched his software business career at Coupa. On Carter’s last day working for Hiro, I “immortalized” that memorable call from Carter in a poem:

130773Rough Guys on the RoadKeith Krach personal photo 

A Brother from Another Mother

Almost exactly one year ago

I got a call from someone I know

Who said that his acting career had gone south

Remembering those first few words out of my mouth

“Carter, that certainly doesn’t make you a zero.”

“You just simply got to go work for Hiro!”

I knew, you two would love one another

Now you call each other brother.

130788BrothersKeith Krach personal photo-kjk


Hiro, the Wing Man

We have had some amazing experiences, from hanging gold medals on champions at the Special Olympics World Games in Austria; to China, where he carried my six-year-old daughter with her broken leg to the top of the Great Wall; to taking batting practice with the San Francisco Giants, to standing shoulder-to-shoulder with three U.S. presidents, and joking about Hiro’s name; to getting tears of joy at DocuSign’s initial public offering. But the times I love the most are the quiet times with Hiro, as he talks about his philosophy of life and the wonderful possibilities the future holds. Perhaps most of all is when he reflects on all the things we have learned together on our journeys.  

Hiro, the Friend

Who is Hiro? I will tell you. He is a person with whom you dare to be yourself. Your soul can be naked with him. He seems to ask you to put on nothing, only to be what you are. He does not want you to be better or worse. When you are with him, you feel like a prisoner who has been declared innocent. You do not have to be on your guard. You can say what you think, so long as it is genuinely you. He understands those contradictions in your nature that lead others to misjudge you. With him you breathe freely. You can avow your little vanities and envies and hates and vicious sparks, your meannesses and absurdities and, in opening them up to him, they are lost, dissolved on the white ocean of his loyalty. He understands. You do not have to be careful. You can abuse him, neglect him, tolerate him. Best of all, you can keep still with him. It makes no matter. He is like you. He is like fire that purges to the bone. He understands. You can weep with him, sin with him, laugh with him, pray with him. Through it all – and underneath – he sees, knows and loves you. A Friend? What is a friend? Just one, I repeat, with whom you dare to be yourself.

Hiro, the Man

Over the last four years I have witnessed Hiro’s impeccable work ethic, ability to build bridges across cultures, build strategic alliances and create new platforms. His results stand on their own, but what brings tears to my eyes when I think of Hiro my hero is his deeply genuine goodness as a man. He is a truly loving and beloved husband, father, son and friend. I have been at his wedding, traveled with him to all corners of the globe and watched him experience the joy of becoming a father, and I know without a shadow of a doubt that his heart and soul are pure. Hiro is the definition of a good man and he is brimming with honor. He lives by the highest moral code and with a personal strength that will propel him to true personal greatness and most importantly: happiness. 

The Journey Continues

Hiro loves to share poems, sayings, famous stories and proverbs with everyone around him. He put one of his favorites, Ithaka in the back of a photo album he gave, as I prepare for my next journey. So, Hiro as I thank you and bid you Godspeed on your next, I have one for you, Hiro, my Hero.

130791Gonna Go FARKeith Krach personal photoIF

-Rudyard Kipling


When things go wrong, as they sometimes will,

When the road you’re trudging seems all uphill,

When the funds are low and the debts are high,

And you want to smile, but you have to sigh,

When care is pressing you down a bit–

Rest if you must, but don’t quit.


Life is queer with its twists and turns,

As every one of us sometimes learns,

And many a fellow turns about

When he might have won if he had stuck it out.

Don’t give up though the pace seems slow–

You may succeed with another blow.


Often the goal is nearer than

It seems to a faint and faltering man;

Often the struggler has given up

When he might have captured the victor’s cup;

And he learned too late when the night came down,

How close he was to the golden crown.


Success is failure turned inside out–

The silver tint of the clouds of doubt,

And you can never tell how close you are,

It may be near when it seems afar;

So stick to the fight when you’re hardest hit–

It’s when things seem worst that you mustn’t quit.





Page created on 2/1/2019 9:41:05 PM

Last edited 2/15/2019 12:52:41 AM

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