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BORN
1950
DIED
2023
Paul Hackleman Obituary
May 15, 1950 - March 1, 2023
Born in Rapid City, SD, to Ruth Kubitschek and JR Hackleman, Paul grew up in many different places as the child of a military family.
He received his BA from the Univ. of the Pacific Callison College, where he studied in India for a year before circumnavigating the globe. He received his Masters in European Intellectual History from the Univ. of Chicago.
After college he returned to the Peninsula, married the love of his life, Rebecca, and began his career with the County of San Mateo working in several different departments before being hired as the Benefits Manager. He headed Benefits for the last 25 years of his 33-year career with the County. He was chosen as the Benefits Manager of the Year by Business Insurance Magazine in 2006 for his bold vision of how benefits could improve work outcomes as well as the lives of employees.
Paul's second career was with SST Benefits where he and his partner helped clients improve their retirement accounts so they could retire with more security. While maintaining two careers, he also taught certificate training classes for the Int'l Foundation of Employee Benefit Plans as well as writing three books on the subjects of Benefits and Retirement Plans for professionals in the field. He was elected to the IFEBP's Executive Board, becoming President in 2018. Paul also served as an elected Board Member for SAMCERA, the County's retirement plan board for 15 years.
Paul was passionate and compassionate. He had a high intellect, loved to read, ran the Boston Marathon for the exercise, enjoyed backpacking in the Sierras, drawing, music, chess and science fiction. But most of all he was a gentleman, polite and always inclusive in everything he did. He was a man in full.
He is survived by his wife, Rebecca Haseleu, his children Nicholaus Hackleman (Annalisa Nielsen) and Laurel Finnegan (John), grandchildren Brandon and Colton.
A Celebration of Life will be scheduled for a later date.
Donations in Paul's memory can be made to Peninsula Open Space Trust or Sempervirens Fund.
To plant trees in memory, please visit the Sympathy Store.
Memories and Condolences
for Paul Hackleman
Susan Ryan
April 17, 2025
Paul left an indelible mark to so many. I was fortunate to work with Paul in the Mental Health Division of the San Mateo County Health Department. He was a wonderful colleague and will be missed by many.
susan bird
March 1, 2025
Paul crosses my mind every one in a while. I remember his insight and openness. I know you miss him every day. He made a difference to many.
Sarah Greenleaf Whittier
March 1, 2024
Dear Rebecca, Laurel and Nick,
I woke up thinking of you all today. I am so grateful to have you in my life, and so grateful for the time I was able to spend with Paul. Take care, my friends.
With love,
Sarah
Bill May
May 13, 2023
I appointed Paul as the Benefits Manager in San Mateo County. It did not take long to figure out that Paul was a very talented individual and superb Benefits Manager. It is with sorrow that I found out of Paul's passing. My sympathy goes out to his wife and children.
Bill May
Susan Cabrera
May 10, 2023
I had the pleasure of working with Paul for many years at San Mateo County. He was a great colleague, very knowledgeable, responsible, and always dapper. He had a great sense of humor, including using the politically correct name of "Hackleperson" at times. Paul was deeply devoted to Rebecca and his family and my condolences go out to them as we miss his amazing and endearing presence and celebrate his wonderful life. God bless Paul, his family, and all of us who
treasure his memory.
Robert "Buff" Rezak
May 9, 2023
My total condolences to Paul's family. My time with the County of San Mateo as a custodian,he was very respectful of everyone, had a great friendly smile. I chatted with him every time I cleaned his department. He will be well missed. He was a great asset to County of San Mateo.
Rich Lee
March 15, 2023
I had the pleasure of working with Paul through SST for many years. He championed post-retirement financial security, was a recognized industry leader, and was a human being of the highest order. My condolences to his family on his passing.
Casey Echarte
March 15, 2023
Paul was a great person to work with, very patient with educating people about benefits, and a very quick wit! He calmed me down when I was nervous about speaking in front of a large room of new County employees, by introducing me as the "dark side of Human Resources" (employee and labor relations)! He was always a hard act to follow!
March 9, 2023
March 9, 2023
Wayne Murphy
March 9, 2023
Paul was very generous of his time and knowledge. A true leader in every sense best described as a modern day renaissance man! During a 2019 conference in Alaska he imparted his empirical knowledge as it related to the awe-inspiring glaziers that appeared before us. He recalled that 15 years earlier when he explored the area with his wife Rebecca those same glaziers were monumental in comparison to what we were witnessing. He reminded us that climate change is a critical challenge and the glaziers are a true benchmark. RIP Paul and thank you for welcoming us Canadians into your circle. You'll be missed.
Derek Dobson, CAAT Pension Plan
March 9, 2023
Paul was always quick with a smile and a genuine interest in other people's success. His strong and quiet intelligence will be greatly missed.
Nancy & Wendell Young
March 8, 2023
Paul lived life to the fullest and was such a joy to be around! We will always remember his stories and passion for learning! His compassion for his friends and family was an inspiration. He always made us feel so special and will miss him terribly! Sending all our love and support to you Rebecca and family
Nicole Piccetti
March 8, 2023
Paul's kindness and welcoming hospitality were a wonderful gift. His passion for all the beauty and peace in nature was contagious and all inclusive. I can see the sparkle in his eye sharing his love of Drakesbad Ranch and Mt. Lassen. Sending you peace and comfort.
Love, Nicole & John
susan bird
March 8, 2023
Paul was one of a kind. He was such a gentle and giving person, ready with a smile, always. I will never forget his insightful stories, beautiful words and truly wonderful welcoming way. I am sorry that he has left us so soon. Rebecca and family you are in our thoughts.
Sempervirens Fund
March 8, 2023
We are so very sorry to hear of Paul's passing. He supported the redwoods for a very long time and will be missed. May you think of him the next time you go outside to enjoy nature.
Tim Sullivan
March 8, 2023
I knew and worked with Paul for many years. A true professional and a great friend. He touched many.
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