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Town Hall Struggles with Turnover

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Hopkinton, typically characterized by its stability and continuity, has been going through an unprecedented phase of transformation. Over the past several months, a number of key employees from vital departments have moved on from their roles, leaving vacant positions in their wake. The Finance organization, in particular, has been significantly affected.

First among these notable departures was Chief Financial Officer (CFO) Tim O’Leary. Having served the town for nearly 5 years, O’Leary was a prudent manager of Hopkinton’s finances, helping to maintain a balanced budget and a favorable credit rating. O’Leary’s departure to take a role as Deputy Director of Financial Services at MIT has left a sizable void within the Finance organization.

O’Leary’s direct reports have departed too. Chris Heymanns, formerly the town’s Treasurer, made a lateral move to become Holliston’s Treasurer. Ben Sweeney, former Town Accountant, is now an Accounting Manager at UMass. Assistant Accountant Stephanie Clifton made a lateral move to Ashland, now serving as their Assistant Accountant.

Preceding O’Leary’s departure was Head of the Department of Public Works (DPW) John Westerling. Westerling’s decision to accept the role as Head of DPW for Natick has been seen as a significant blow to Hopkinton’s public works agenda, particularly while it grapples with water scarcity, PFAS contamination and the ongoing Main Street construction project.

Adding to the series of departures, Fire Chief Bill Miller, a veteran with over 23 years of service in the Hopkinton Fire Department, stepped down this month to accept the role as Fire Chief in Bellingham.

The Police department has several unfilled positions, including Deputy Chief and Lieutenant.

After 9 years at the Hopkins School, Principal Vanessa Bilello left for the Lawrence School in Brookline, and Director of Student Services Karen Zaleski left for Weston Public Schools.

Finally, Jay Guelfi, Director of Parks and Recreation, announced his retirement. Guelfi played a crucial role in expanding Hopkinton’s green spaces and recreational facilities and his departure could potentially impact ongoing and future park projects within the town.

Excluding seasonal workers and substitute teachers, the town has lost 35 employees in the past 12 months.  

>> Review the Compensation worksheet for all town employees

These back-to-back departures have raised questions about the town’s ability to retain top talent and have added pressure on the remaining leadership to find worthy successors.

With the CFO position vacant, the responsibilities for the role fall to Town Manager Norman Khumalo, as he oversees the finance department. Khumalo also has full administrative authority over DPW and Human Resources, with dotted lines to Parks & Recreation and the Library. The fire & police chiefs report directly to the Select Board.

One underlying reason for turnover may be that salaries for town employees have not kept pace with our neighbors. According to the FY2022 Town of Hopkinton Compensation schedule, Assistant Account Stephanie Clifton was paid $62,294 in 2022. In her new job in Ashland she is paid more than $83,000 annually for a 37 hour work week. Although not confirmed, O’Leary, Sweeney, Westerling, and Miller all left for jobs that likely pay more.

It is unclear when many of these critical vacancies will be filled. While the job posting for the Assistant Town Accountant and DPW Director are available on the town website, many others are not. 

As Hopkinton navigates this challenging period of transition, the town’s residents will be watching closely to see how new appointments perform in their roles and shape the town’s trajectory. Amid all the changes, one thing is clear – the coming months will be instrumental in defining Hopkinton’s future.

This article was corrected on 5/26/2023. The true number of departures in the last 12 months is 35, not 34 as originally stated.


  1. Is it really that surprising? There are a number of major issues pressing this community. Presently you have an unsustainable population growth that education and support services cannot support. Legacy Farms was submitted as 1-4 child to home ratio, it’s nearly triple that and growing. Marathon over capacity in one year! A top 5 school system shouldn’t have 23 kids per class, converting art rooms to class rooms. The construction project downtown is a joke. Nothing is being gained. An extra lane on 85…wow…that’s not going to relieve traffic. The raised bike lane was unnecessary when a traffic line would have be sufficient, but the consulting company earned more money. Who has any trust that the new 3-4-5 school being built is actually a good idea when all educators recommended staying with a 3-4 school to replace Elmwood. I don’t.

    Oh and there’s the long term issues of PFA’s in the drinking water and LNG plant beyond life expectancy ready to level half the town…

    But hey, that school committee s*** show was awesome.

    Yeah no idea why employees are bailing ASAP.

    • Joshua, not sure if you have kids in the schools or not, or where you are getting your information, but the current Elmwood is a 2-3 school. There is no 3-4 school.And the proposal calls for a 2-3-4 school, not a 3-4-5 school.

  2. Nothing too good and no amount of money too much for the school children of Hopkinton.

    No money for seniors, town employees, infrastructure…but plenty for boondoggles. I could go on and on.

    But please…more money for the school children.

    I am so glad I moved out of Hopkinton.

    • No more money for schools when they can’t spend all the money they thy waist it on bull crap just to spend. Highway,fire and PD Do the same.

  3. This is concerning “With the CFO position vacant, the responsibilities for the role fall to Town Manager Norman Khumalo, as he oversees the finance department. Khumalo also has full administrative authority over DPW and Human Resources, with dotted lines to Parks & Recreation and the Library. The fire & police chiefs report directly to the Select Board.” as Norman has actively been trying to take another role in a different town/city. I hope stability is on the horizon

  4. I recently applied for a position in this Town–I felt like I was applying for a job in 2004. They are still using paper applications–in fact they ‘require’ paper applications! The process was so long and convoluted that I ended up getting a job in another town. I am so glad that I didn’t get the job after reading this article.

  5. Maybe we should be looking at the Town Manager??? It all comes from the top! Why did all these people leave really??? The Select board needs to look into this.

    • you’re getting hot. Look at the turnover since the Town Manager came on board. This has little to do with salaries and everything to do with leadership.

  6. I’m another glad to be gone. You all realize that you vote on staff salaries at Town Meeting right? It’s part of the budget. The budget generally passes in 30 seconds and then most of you complain about things like trees and engage in petty squabbles about trails in the woods as if it’s a national emergency. Clearly there’s no confidence in Khumalo, but you folks really need to get your act together as a town. No one cares that the marathon starts there and public schools do not need to be college campuses.

  7. The buck should stop at the Town Manager. How can you have a motivated staff if he actively looking to leave? He has been a disengaged manager for years. Now his staff is leaving. It is time for Mr. Khumalo to leave. We need fresh ideas and stability at the top

  8. It’s not just the salary, it’s the culture at Town Hall. Leadership gives lip service to valuing employees, and then brags about having a policy of paying 75% of the typical going rate. There’s a responsibility to the taxpayers to be conservative with the budget, but at what other costs? How much is it going to cost to fill these vacant positions and train new people, and how much lost production will happen while they wait to find someone willing to join the fray?

  9. Recently, Germany has officially entered recession. The EU will follow shortly. The USA is technically already in recession and will follow the EU. The too big to fail banks in the USA are gobbling up the assets of the failed banks and leaving the liabilities to the taxpayers. The regional banks in the USA are heavily invested in Commercial Real Estate which is collapsing. The big box retail stores are struggling. The consumer (60% of economic activity in the USA) is tapped out and using credit cards to buy necessities at an alarming rate. Our food supplies are being curtailed in many ways resulting in higher prices and potential shortages. Student loan repayments will begin shortly and add an average of $400 USD/month to indebted individuals. The political system in the USA is broken. The banking system in the USA is a fractional reserve system. That means for every $1 USD deposited, the bank my lend out $10 USD. The FDIC is no different. Within the system, there is no place to hide. CBDC’s (Central Bank Digital Currency) will be proffered by the system as the savior of our economy but will result in total government control of our lives. How much we spend and when and on what will be closely scrutinized by the powers that are in control and outliers will have their freedoms curtailed. No wonder we are seeing the rats deserting the sinking ships.

  10. I am also a former employee who will remain anonymous for the sake of my current position.
    It’s time for a complete overhaul of town hall. Time for Khumalo to leave and take Casey with him. Start fresh. Hopefully the select board reads this.

    • Another former town employee. OMG so true, the micromanagement is intense.
      Norman Khumalo & Maria Casey need to GO!

      • Khumalo is just fine. I’m sure he’s at the lower end of the pay spectrum too. Speaking of micromanagement have you seen the way the select board micromanages him? No wonder everybody is looking to leave.

  11. Past employee of 20years was SO happy to retire. I am a resident of Hopkinton since 1971 can’t wait to sell and get out of town. Sad. Norman must go and it’s good Westerling left the town got lucky there.

  12. Not to mention a bunch of administrators who left last year at this time including an athletic director (another one this year too)

  13. As they say “the fish rots from the head down”. Norman is a micro manager who wants “yes men” in department head roles. Westerling was terrible at his job and spent more time traveling out of state and working for the APWA (American public works assoc) than for the residents. Multiple out of state trips paid for by tax payers. Why would the public works director need a professional headshot photo? It’s no wonder so many from finance have left because he asks things from them that are either unsustainable or they are uncomfortable with doing. This article only scratch’s the surface of systemic mismanagement. It mentions nothing of how many rank & file employees have left.

  14. Personal attacks such as the ones in this thread are a really good example of why HopNews should not allow anonymous comments. I don’t buy the argument that it’s not possible to verify identity. Making the name and address fields required is easy enough to do, and the comments are moderated anyway so a quick address lookup should be easy enough to accomplish. If someone signs a comment with someone else’s name and address, the crowd can police it. It may not be a perfect system but it must surely be better than this. As it is, for this or any other article, how do we know that all the personal attacks aren’t coming from the same one or two authors who want to create a false narrative? Fake news can be very destructive to a small town. If you believe something, you should stand by it and sign your name to it.

    I have my doubts about whether this comment will get printed, but let’s take a shot.

    • There’s about a dozen comments sharing different experiences as well as the article reporting on half a dozen other people departing from high ranking town jobs…. If you think it’s the same ‘1 or 2 authors’ then I don’t know what to say. I understand it may be tough to realize that the seemingly ‘perfect’ town isn’t run so perfectly

    • Retaliation is a real concern for employees of this town. Just look what you people do to your own neighbors when you disagree politically. Nobody is going to use their real names because they will be in the unemployment line next. Do you realize that employees were threatened with disciplinary action and or dismissal if they affixed a small remembrance sticker to a town vehicle for a 30+ year employee and suicide victim? This management is heartless.

  15. Was tired of being grossly underpaid in comparison to area departments and Norman and Town Hall clearly did not care that we had people leaving in masses. Viewed only as ‘employee #s’ and not valued as people

  16. Ms. Groves. Municipal government is small. If we were to give our names our current positions could suffer. We are all trying to get the tax payers to finally see beyond the veil. Many of us still live in town and have family members still employed with the Town. We are commenting for them!! Read between the lines!

  17. There seems to be a cultural and compensation issue that Hopkinton CAN afford to address, if we can pay for the most elaborate bike lanes ever built. There is a very high cost of turnover and this level of brain drain, all at once, will take a while to rebuild from. It also seems unfair to both the taxpayers and voters to allow Norman Khumalo to become too “powerful” due to vacancies. This is suspect alone. We need qualified, paid employees in these roles, who are allowed to do their jobs on our behalf, without our select board micromanaging or otherwise interfering with professional people who have already been vetted. Boards do not have a role in micromanagement. Boards are designed for high level oversight based on high level reporting of outcomes. Oversight should stay out of daily operations in general. I do not play in town politics here, but it does seem just from reading the local news that now Mr. Khumalo has far too much control over matters that Professionals from town should be managing. How will the handoff go now? The By-Laws should be revisited to prevent this from happening again.

  18. Former Town employee here. The comments about the Town Manager are spot on. When former select board member Tedstone was running he ran on the platform of finding out what was going on. As soon as he got in though he never once brought it up that I saw. That’s how long this has been going on.

    • Tedstone is as townie as it gets. He’s a great man that did not let political parties mar his judgment on issues. I’m sure he was getting things done behind the scenes with whispered conversations at the Nell or startline.


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