Here's to Dennis... colleague, mentor, friend.  I met Dennis in 1986 when I was a third-party OEM to Timberline.  He was a steady professional influence... someone I admired and respected. Through the years, we shared our perspectives from different disciplines in our industry, compared memories from our college football experiences, expanded our horizons time and again as the products we represented advanced with new technologies, and, well, became good friends. I'm disappointed we didn't get to golf together in retirement, disappointed that we won't share another 'old fashion', disappointed that he didn't get to live out a lengthy retirement that he well deserved.  But I am grateful for the time that I and many others got to spend in his presence... here's to Dennis.

...and a lifetime of tradeshow presentations.  

Here's to Dennis.

...pictured here in our tradeshow booth with top execs from our industry partner, Procore.

... out to dinner with special ISV partner Operix at a trades show.

Very sad to learn that Dennis is gone.  Dennis was a solid teammate that always had a kind word for every former Badger.  So many memories on the field and off.  Godspeed my friend!

We at Riskcast are deeply saddened to hear of Dennis’ passing. Dennis was a trusted colleague and a sincere supporter of our company. As a young startup, it wasn’t always easy finding our place in the industry, but Dennis welcomed us without hesitation. He offered us honest feedback, free of bias or pretense—never sugar-coated, always thoughtful. That rare combination of candor and encouragement left a lasting impact on our team.

Our hearts go out to his family and loved ones during this difficult time. Please accept our deepest condolences. Dennis will be remembered with great respect and gratitude.

I am so sorry to hear of Dennis' passing - way too early.  I worked with Dennis for over 25 years at Timberline and Sage and have the highest respect for him.  Truly a man of integrity, kindness and intelligence.  Please accept my condolences to the many family members he's left behind.

It is a challenge to capture the essence of Dennis with words alone, for his presence was as generous as it was profound. I first met Dennis over thirty years ago, and from those earliest days, he became an inspiring mentor—his deep industry expertise and encyclopedic command of our software left a lasting impression on everyone he guided. Dennis’s professional journey was marked by numerous accolades that reflected his unwavering dedication and pursuit of excellence. Yet, his legacy extends far beyond titles and awards.
Dennis poured his time and wisdom into shaping those around him. He mentored countless colleagues, always eager to share his insights or patiently walk someone through a challenge. One memorable instance was when he stayed late with a new team member, not just explaining a technical issue but turning it into a lesson about perseverance and curiosity—qualities he embodied in every aspect of life. He never just gave you the answers but forced you to find them, guiding the way. 
Outside of work, Dennis’s competitive spirit shone brightly on the golf course, and his excitement for Badger sports was infectious, drawing friends and family together for shared moments of joy. Above all, the heart of Dennis’s world was his family. To his beloved wife Jan,  Kate and Matt, and cherished grandchildren Trinity and Connor, you have my deepest condolences. May you find comfort in the many lives Dennis touched and in the enduring light he brought to your lives and to all of ours.  He will be greatly missed.

I was deeply saddened to hear of Dennis's untimely passing. He was a legend in every sense of the word.

I began my career at Timberline in 1996. At that time, Dennis was already a key figure on the leadership and development team that had created what was widely recognized as the most powerful and respected software platform in the construction industry. That same team helped elevate Timberline into a dominant and highly trusted brand—so influential that, even though the name officially disappeared over 20 years ago, Timberline is still spoken of with admiration and nostalgia across the industry.

Years later, when the parent company set out to modernize and rebuild the platform to meet a new era of competition, they made one of their wisest decisions: they brought Dennis back. Once again, he played a critical leadership role in developing and launching a remarkably robust and forward-thinking system.

Dennis was more than just brilliant—he was gracious, thoughtful, and consistently encouraging. Always positive, always approachable, and always sharp. I’m truly grateful to have had the opportunity to work with him and learn from him. I’ll miss seeing his familiar face at industry events and conferences. His legacy will live on in the work he shaped and the people he inspired.

The news of Dennis's passing has left me saddened. He was an outstanding individual. Always willing to extend a friendly greeting. His presence will be greatly missed by the men's group at Coyote Ridge.

My heart is saddened with the loss of Dennis. He started out after college in the Timberline Chicago region when Nace Mullin was the Regional Manager. This is where I met Dennis as he did my Install’s for Timberline. Dennis was also instrumental in helping BuilderMT get integrated with Timberline, which was huge for BuilderMT.  I am grateful for the opportunity to know him, Jan and Katie   Rest in Peace Dennis. You will be missed!

My heart is heavy as I think of my brother - a beloved husband, father, grandfather, brother, uncle and friend.  He left us far too soon, but not without leaving his permanent mark on our hearts and lives.  To know Dennis was to know his quiet but wise nature and his love for his family, his Wisconsin Badgers, golf, and travel.  In his honor I will raise a glass to him, cheer on his Badgers, work on my golf swing, and keep his family close in my heart.

I'm so sorry for your lose.  Dennis was my boss for a few years and we worked together in some way for over 20 years.  He was always so nice to be around.  He always had a kind word and a smiling face.  But what sticks with me the most is the first time I met him.  It was his huge hands when I went to shake it - like a bear paw.

I'll miss saying hi to you Dennis.

Jan and family,

We are heartbroken to hear of the sudden loss of Dennis.  He was like clockwork with his 7am cleanings (even in retirement!) which made us smile.   We often caught up on his golf game and where he was traveling next.  A true joy to have around.  He will be missed.  A life well lived.  Prayers for peace during this time.

Dr. Penchan, Dr. Scaggs, Angela, and the entire team at Josey Lane Dentistry

Dinner October 2024 - The launch of CRE UK

Dennis was a wonderful person.  We worked with him for many years.  So, so sad to see that he passed.
Diane Sector

I am so sorry for your loss.  I got a chance to be on a Sage panel with Dennis last year and get to know him a little bit.  He was so generous with his time and knowledge.  Peace to his family and friends.

Condolences from Australia.  Dennis was well respected here in Oz as part of Timberline community.   Dale Ipsen

Kate, 
I am so sorry to hear of the unexpected loss of your Dad. It is extra hard to lose our loved ones at any time, but even harder when it is so sudden without hint or warning. 
You, your mom and the entire family will be in our prayers as you navigate the days ahead. 
May God’s peace surround you all and give comfort.

Jan and family,
I’m so sorry to hear of Dennis’ sudden passing.  I didn’t know him well - seeing him occasionally on the neighborhood golf course late in the afternoon or evening, or putzing around in the yard.  You are all in my prayers during this difficult time. Rest in peace, Dennis.  Love, Tony and Gena Harmon.

In a bit of shock, we lost a beautiful soul in our family. My Uncle Dennis was a charismatic man. An amazing husband, father, brother, son, and uncle to his family. I had the chance to get to know him even more this year. I wrote a poem to celebrate those memories of him.

Dear Uncle Dennis, 

I’ll miss you, Uncle. 
Kind and warm-hearted. 
What great wittiness and gift of gab! 
An ode to the competitive spirit!
We shook under poker faces, clenching our dimes. 
Childhood ski trips and family get togethers. 
Smiles and soft-hearted jabs to get the party started.

I’ll miss you, Uncle. 
Bonding over regaled tales -
Your mom marching in front of a crowd to cheer you on. 
How mischief ensued whenever you and your siblings got together. 
How some cute lady stole your hat and you threw her over your shoulder to get it back…
…and asked for her number later, too.
Heck, you ended up marrying her, because that’s what lovebirds do. 

I’ll miss you, Uncle.
You had Mimi’s smile and Goompa’s laugh.
I find comfort in knowing you’re in their arms.
You’re the piece of the Stejskal sibling puzzle that has gone missing in our lives. 

I’ll miss you, Uncle. 
So thankful to have known you.
It’s ‘au revoir,’ not ‘goodbye,’
I’m sending a paper lantern in the sky. 
Rest in peace, my dear Uncle. 
We all love you.

OBITUARY

Dennis James Stejskal

May 30, 1956 – July 15, 2025

Rhoton Funeral Home

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